Dichloromethane → (2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol

HRID 1026562Notes

Reaction equation

HRID 1026562 reaction equation
ClCCl.[CH2:4]([OH:9])[CH2:5][C@@H:6]([OH:8])[CH3:7].[C:10]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])([CH3:12])[CH3:11].[Cl-].[NH4+]>C(N(CC)CC)C>[Si:14]([O:9][CH2:4][CH2:5][C@@H:6]([OH:8])[CH3:7])([C:10]([CH3:13])([CH3:12])[CH3:11])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 446973(+)-1,3-Butanediol

Product 1

HCID 58005224(2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Under ice cooling, to a dichloromethane solution (20.0 ml) of (S)-1,3-butanediol (519 mg) were added triethylamine (1.04 ml) and tert-butylchlorodiphenylsilane (1.63 ml), followed by stirring at room temperature overnight. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford (2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol (1.69 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-25728101a12f47a6b6ac19b9099b809e
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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