tert-Butyldimethylsilyl chloride → HCID 12502494, compound

HRID 256489Notes

Reaction equation

HRID 256489 reaction equation
Cl[Si:2]([CH3:8])([CH3:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[Cl:9][C:10]1[C@@H:14]([OH:15])[CH2:13][C:12](=[O:16])[CH:11]=1>CN(C)P(=O)(N(C)C)N(C)C.O>[Cl:9][C:10]1[C@@H:14]([O:15][Si:2]([CH3:8])([CH3:7])[C:3]([CH3:6])([CH3:5])[CH3:4])[CH2:13][C:12](=[O:16])[CH:11]=1

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 12653989HCID 12653989, compound

Product 1

HCID 12502494HCID 12502494, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

Chlorodimethyl-t-butylsilane (485 mg, 3.22 mmol) was added over 5 min to the crude (4S)-enone (7) (247 mg) in hexamethylphosphoric triamide (2 ml) at 0°. After stirring at 4° for 20 h the solution was diluted with water (10 ml) and extracted with ether (3×10 ml). The combined ether extracts were washed with water (3×10 ml), dried (MgSO4) and evaporated to give a pale yellow oil (456 mg) which was chromatographed on a column of silica gel (25 g) with methylene dichloride-methanol (50:1) as eluant. The (4S)-enone (8; R1 =Me2ButSi) [243 mg, 61% from the 3,5,5-trichloro-4-hydroxycyclopent-2-en-1-one (6)] was obtained as a colourless oil, [α]35225 +1050° (c. 9.14×10-2, hexane), [α]23425 -16,140° (c 1.83×10-3, hexane), [θ]33325 +6700° (c 9.14×10-2, hexane), [θ]22225 -80,330° (c 1.83 ×10-3, hexanel). (Found: C, 53.65; H, 7.95; Cl, 14.6. C11H19ClO2Si requires C, 53.55; H, 7.75; Cl, 14.35%)

Workup

  1. extractionextracted with ether (3×10 ml)
  2. washThe combined ether extracts were washed with water (3×10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-5dfa369f26954031b5d9a38f082293a2
Source dataset
uspto-grants-1987_10
Patent number
US04703127

Reaction notes

Loading…