Dichloromethane → (S)-5,9-dimethyl-9-trimethylsilanyloxy-decanal

HRID 1740546노트

반응식

HRID 1740546 반응식
[OH:1][C:2]([CH3:14])([CH3:13])[CH2:3][CH2:4][CH2:5][C@H:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH:10]=[O:11].C(Cl)Cl.[Si:18](Cl)([CH3:21])([CH3:20])[CH3:19]>CN(C1C=CN=CC=1)C.CCN(CC)CC>[CH3:12][C@@H:6]([CH2:5][CH2:4][CH2:3][C:2]([CH3:13])([O:1][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])[CH2:7][CH2:8][CH2:9][CH:10]=[O:11]

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 6397ChlorotrimethylsilaneHCID 54287074(S)-9-hydroxy-5,9-dimethyl-decanal

생성물 1

HCID 53652168(S)-5,9-dimethyl-9-trimethylsilanyloxy-decanal

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8471Triethylamine용매

실험 절차

3.10 g of (S)-9-hydroxy-5,9-dimethyl-decanal was dissolved in 60 ml of abs. CH2Cl2 and treated successively at 0° with 57 mg of DMAP, 7.0 ml of NEt3 and 3.1 ml of TMS-Cl. The reaction mixture was kept for 30 minutes at RT and then poured onto crushed ice, extracted twice with ether, washed twice with water and brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=95/5) yielded 3.90 g of (S)-5,9-dimethyl-9-trimethylsilanyloxy-decanal as colorless oil, 98.6% pure according to GC.

후처리

  1. additionpoured
  2. customonto crushed ice
  3. extractionextracted twice with ether
  4. washwashed twice with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-537ccd15bdf54b2f9ef0c9e07eacbbc7
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05969190

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