Sodium borohydride → 1-(1-Adamantyl)-2-(3,4-dichlorophenylthio)ethanol

HRID 259310Notes

Reaction equation

HRID 259310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][C:11]([C:13]23[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+]>CO>[C:13]12([CH:11]([OH:12])[CH2:10][S:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:21]3)[CH2:20]1)[CH2:22]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 214240441-Adamantyl 3,4-dichlorophenylthiomethyl ketone

Product 1

HCID 214240851-(1-Adamantyl)-2-(3,4-dichlorophenylthio)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-adamantyl 3,4-dichlorophenylthiomethyl ketone (1.2 g.) in 250 ml. of methanol is treated with excess sodium borohydride with stirring and ice cooling. When reduction is complete, the solvent is removed, 50 ml. of water is added and the product is extracted with ether. The combined extracts are washed with water, dried over magnesium sulfate and evaporated to dryness to yield 1-(1-adamantyl)-2-(3,4-dichlorophenylthio)ethanol.

Workup

  1. customthe solvent is removed
  2. additionof water is added
  3. extractionthe product is extracted with ether
  4. washThe combined extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6d4fc1930ae24377a9489563ac1c927f
Source dataset
uspto-grants-1977_07
Patent number
US04036975

Reaction notes

Loading…