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

HRID 1740546ノート

反応式

HRID 1740546 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-537ccd15bdf54b2f9ef0c9e07eacbbc7
出典データセット
uspto-grants-1999_10
特許番号
US05969190

反応ノート

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