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

HRID 1194784노트

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HRID 1194784 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-841ab16241fb42ebbba39a4d96006fe8
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04816476

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