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

HRID 1026562ノート

反応式

HRID 1026562 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-25728101a12f47a6b6ac19b9099b809e
出典データセット
uspto-grants-2014_05
特許番号
US08729095B2

反応ノート

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