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

HRID 2352278ノート

反応式

HRID 2352278 の反応式
[S:1]1[C:5]([C:6](OC)=[O:7])=[CH:4][C:3]2[S:10][CH:11]=[CH:12][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[OH:7][CH2:6][C:5]1[S:1][C:2]2[CH:12]=[CH:11][S:10][C:3]=2[CH:4]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 2739788Methyl thieno(3,2-b)thiophene-2-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 14601398(Thieno(3,2-b)thiophen-2-yl)methanol収率 98.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-dc1de8bd2f73480087c29c366091000c
出典データセット
uspto-grants-1989_10
特許番号
US04876271

反応ノート

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