Water → (Thieno(3,2-b)thiophen-2-yl)methanol

Participants

Reaction Steps

A solution of methylthieno[3,2-b]thiophene-2-carboxylate (6) (37.04 g., 186.9 mmoles) in ether (850 mL) was added at a rapid drip (1 hr. 45 min.) to a suspension of lithium aluminum hydride (14.18 g., 373.7 mmoles) in ether (500 mL) which had been cooled in an ice-water bath. After the addition was completed, the mixture was stirred at room temperature for three hours. The reaction was worked up by cooling in an ice-water bath with successive dropwise addition of water (14 mL), 15% aqueous sodium hydroxide (14 mL) and water (42 mL) with vigorous stirring. Vigorous stirring was continued until the salts are well granulated. The ether solution of the product was decanted and the salts washed further with ether. The combined ether solutions were dried (MgSO4), filtered, and the solvent evaporated in vacuo to leave 31.4 g of 2-hydroxymethylthieno[3,2-b]thiopene (7) (mp 91° to 93° C.) which was used in the next step without purification. A small sample was recrystallized from hexane for analysis (mp 93°-94° C.).

Provenance & Evidence