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

HRID 1740546Notes

Reaction equation

HRID 1740546 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-537ccd15bdf54b2f9ef0c9e07eacbbc7
Source dataset
uspto-grants-1999_10
Patent number
US05969190

Reaction notes

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