Ammonium Chloride → HCID 22648514, compound

HRID 393118Notes

Reaction equation

HRID 393118 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][C:12]([S:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:16])[CH2:13][CH2:14][CH3:15])C.[NH4+].[Cl-]>CCOCC>[CH2:18]([S:17][C:12]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10][OH:9])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 53885188HCID 53885188, compound

Product 1

HCID 22648514HCID 22648514, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At a temperature of 0° C. to a suspension of 6.8 g (0.18 mol) of LiAlH4 in 200 ml of Et2O was slowly added 50.0 g (0.18 mol) of (rac)-3-benzylsulfanyl-3-methyl-hexanoic acid ethyl ester of step (b) under stirring such that the temperature did not exceed 10° C. Stirring was continued for 1 h and under cooling acetone and then 400 ml of a saturated NH4Cl solution was slowly added. The reaction mixture was extracted three times with 200 ml of Et2O, the combined organic layers were dried over Na2SO4 and concentrated in vacuo and gave 40.8 g of a yellowish oil. After drying in high vacuo (0.05 mbar/150° C.) 32.5 g (75%) of (rac)-3-benzylsulfanyl-3-methyl-hexan-1-ol in the form of a yellowish oil was obtained.

Workup

  1. customdid not exceed 10° C
  2. stirringStirring
  3. extractionThe reaction mixture was extracted three times with 200 ml of Et2O
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6a18d1a9bf342fa8226c3cd0a7bf831
Source dataset
uspto-grants-2004_10
Patent number
US06805893B2

Reaction notes

Loading…