Ammonia → 3-methyl-3-sulfanylhexan-1-ol

HRID 393119Notes

Reaction equation

HRID 393119 reaction equation
C([S:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])C1C=CC=CC=1.N.CCO.Cl>CCOCC>[SH:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 22648514HCID 22648514, compound

Product 1

HCID 101300393-methyl-3-sulfanylhexan-1-olYield 112.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At a temperature of −78° C. to a solution of 16.0 g (67.1 mmol) of (rac)-3-benzylsulfanyl-3-methyl-hexan-1-ol of step (c) in 200 ml of Et2O was added from a cylinder about 200 ml of NH3. Then pieces of Na (ca. 4.0 g) were added until the reaction mixture remained blue for more than 20 min. The blue colored mixture was allowed to warm up to room temperature overnight and EtOH was added until the blue color disappeared. The mixture was then acidified with about 2.7 M of HCl, and extracted three times with 150 ml of Et2O. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. Distillation of the crude product at reduced pressure (40 mbar/130° C.) gave 11.2 g (73%) of (rac)-3-mercapto-3-methyl-hexan-1-ol in form of a colorless oil.

Workup

  1. waitremained blue for more than 20 min
  2. extractionextracted three times with 150 ml of Et2O
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. distillationDistillation of the crude product at reduced pressure (40 mbar/130° C.)

Sources & evidence

ORD record
ord-909b08e7ff414e76ac8f8ebe32d84b7f
Source dataset
uspto-grants-2004_10
Patent number
US06805893B2

Reaction notes

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