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

HRID 1194784Notes

Reaction equation

HRID 1194784 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-841ab16241fb42ebbba39a4d96006fe8
Source dataset
uspto-grants-1989_03
Patent number
US04816476

Reaction notes

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