Imidazole → tert-butyl (3S,7R,8S)-5-oxo-3-(triethylsilyloxy)-4,4,8-trimethyl-7-(2,2,2-trichloroethoxy-carbonyloxy)-10-undecenoate

HRID 2296868Notes

Reaction equation

HRID 2296868 reaction equation
[O:1]=[C:2]([CH2:16][C@@H:17]([O:23][C:24]([O:26][CH2:27][C:28]([Cl:31])([Cl:30])[Cl:29])=[O:25])[C@@H:18]([CH3:22])[CH2:19][CH:20]=[CH2:21])[C:3]([CH3:15])([CH3:14])[C@@H:4]([OH:13])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].N1C=CN=C1.[CH2:37]([Si:39](Cl)([CH2:42][CH3:43])[CH2:40][CH3:41])[CH3:38].O>CN(C)C=O>[O:1]=[C:2]([CH2:16][C@@H:17]([O:23][C:24]([O:26][CH2:27][C:28]([Cl:29])([Cl:30])[Cl:31])=[O:25])[C@@H:18]([CH3:22])[CH2:19][CH:20]=[CH2:21])[C:3]([CH3:14])([CH3:15])[C@@H:4]([O:13][Si:39]([CH2:42][CH3:43])([CH2:40][CH3:41])[CH2:37][CH3:38])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 13819ChlorotriethylsilaneHCID 60003397tert-butyl (3S,7R,8S)-5-oxo-3-hydroxy-4,4,8-trimethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoate

Product 1

HCID 86586621tert-butyl (3S,7R,8S)-5-oxo-3-(triethylsilyloxy)-4,4,8-trimethyl-7-(2,2,2-trichloroethoxy-carbonyloxy)-10-undecenoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl (3S,7R,8S)-5-oxo-3-hydroxy-4,4,8-trimethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoate (1.7 g), imidazole (0.48 g), and triethylsilyl chloride (0.68 g) in 5 mL of dimethylformamide is stirred for 2 hours at ambient temperature, then poured into water and extracted with ether. The extract is washed with sat. aq. NaCl, dried over MgSO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

Workup

  1. extractionextracted with ether
  2. washThe extract is washed with sat. aq. NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe product is purified by chromatography on SiO2

Sources & evidence

ORD record
ord-5c0ba393c4cb4d90bb7ca8def80be6b9
Source dataset
uspto-grants-2002_12
Patent number
US06489314B1

Reaction notes

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