Ammonium Chloride → HCID 22648514, compound

HRID 397242Notes

Reaction equation

HRID 397242 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, compound

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 9 (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 9 (75%) of (rac)-3-benzylsulfanyl-3-methyl-hexan-1-ol in 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-a1f9c2be44c142cabf327b99b1b64466
Source dataset
uspto-grants-2003_08
Patent number
US06610346B1

Reaction notes

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