Sodium borohydride → 4,5,6,7-Tetrahydro-alpha,4,4,7,7-pentamethylbenzo[b]thiophene-methanol

HRID 2106738ノート

反応式

HRID 2106738 の反応式
[C:1]([C:4]1[S:8][C:7]2[C:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[CH3:2][CH:1]([C:4]1[S:8][C:7]2[C:9]([CH3:15])([CH3:16])[CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH:5]=1)[OH:3]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 230492331-(4,4,7,7-Tetramethyl-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)ethan-1-one

生成物 1

HCID 867402444,5,6,7-Tetrahydro-alpha,4,4,7,7-pentamethylbenzo[b]thiophene-methanol収率 92.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

21.7 g of 2-acetyl-4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thiophene are dissolved in 250 ml of ethanol and the solution is treated gradually with 5.5 g of sodium borohydride. The mixture is left to come to room temperature and is stirred for a further 2 hours. The mixture is poured on to ice, extracted with ether, the organic phase is washed once with saturated sodium chloride solution, dried and evaporated. The crude product is filtered over silica gel (eluting agent hexane/ether 3:1) and recrystallized from hexane. There are obtained 20.2 g of 4,5,6,7-tetrahydro-α,4,4,7,7-pentamethylbenzo[b]thiophene-methanol in the form of colorless crystals, m.p. 53°-55° C.

後処理

  1. waitThe mixture is left
  2. customto come to room temperature
  3. additionThe mixture is poured on to ice
  4. extractionextracted with ether
  5. washthe organic phase is washed once with saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. filtrationThe crude product is filtered over silica gel (eluting agent hexane/ether 3:1)
  9. customrecrystallized from hexane

出典と根拠

ORDレコード
ord-c5660ac2fec1449888cf9a9287b7b15e
出典データセット
uspto-grants-1990_06
特許番号
US04931458

反応ノート

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