6 dimethylbicyclo 3 1 1 heptan 2 yl 4 4 hydroxybutyl benzene sulfonamide in example 18 step d the similar process afforded the title compound in 60 yield as pale paste 1 h nmr cdcl 3 7 05 d 2h j 8 31 hz 6 74 d 2h j 8 16 hz 3 93 3 84 m 4h 2 53 2 15 m 16h 1 15 s 3h 0 99 s 3h step a 4 6 methoxybenzofuran 2 yl ethynyl phenyl acetate when 4 iodophenyl acetate and 2 ethynyl 6 methoxybenzofuran were substituted for 4 bromo n 6 6 dimethylbicyclo 3 1 1 heptan 2 yl benzene sulphonamide and but 3 yn 1 ol respectively in example 18 step b the similar process afforded the title compound in 56 yield as creamy paste 1 h nmr cdcl 3 7 56 d 2h j 8 67 hz 7 41 d 1h j 8 58 hz 7 10 d 2h j 8 7 hz 6 97 d 1h j 1 92 hz 6 9 s 1h 6 88 bd 1h j 8 61 hz 3 85 s 3h 2 3 s 3h step b 4 2 6 methoxy 2 3 dihydrobenzofuran 2 yl ethyl phenol when the product of step a was substituted for n 6 6 dimethyl bicyclo 3 1 1 heptan 2 yl 4 4 hydroxybut 1 ynyl benzenesulphonamide in example 18 step c the similar process higher pressure of h 2 afforded the title compound in 96 yield as creamy paste 1.