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

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.).

1. temperaturehad been cooled in an ice-water bath
2. additionAfter the addition
3. stirringVigorous stirring
4. customThe ether solution of the product was decanted
5. washthe salts washed further with ether
6. dry with materialThe combined ether solutions were dried (MgSO4)
7. filtrationfiltered
8. customthe solvent evaporated in vacuo

ORD record

ord-dc1de8bd2f73480087c29c366091000c

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04876271