Ethyl 6-(Chloroformyl)hexanoate → Ethyl 7-oxo-7-phenylheptanoate

HRID 2250565Notes

Reaction equation

HRID 2250565 reaction equation
Cl[C:2](=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C[Si](C)(C)C1S[CH:18]=[CH:19]N=1>ClCCl>[O:13]=[C:2]([C:19]1[CH:18]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 543232Ethyl 6-(Chloroformyl)hexanoateHCID 5884532-Trimethylsilylthiazole

Product 1

HCID 11107694Ethyl 7-oxo-7-phenylheptanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 7-chloro-7-oxoheptanoate (1.31 g) in dichloromethane (25 mL) was added a solution of 2-(trimethylsilyl)-1,3-thiazole (500 mg) in dichloromethane (5 mL) under nitrogen. After stirring for 3 hours, the reaction was quenched by adding saturated sodium bicarbonate (5 mL). The mixture was partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate (30 mL), and the organic layer was washed with brine, dried over magnesium sulfate, and evaporated to give a colorless oil. Flash silica gel column chromatography eluting with ethyl acetate-hexane=1-10 to 2-5 afforded ethyl 7-oxo-7-(1,3-thiazol-2-yl)heptanoate as a colorless oil (778 mg).

Workup

  1. customthe reaction was quenched
  2. additionby adding saturated sodium bicarbonate (5 mL)
  3. customThe mixture was partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate (30 mL)
  4. washthe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a colorless oil
  8. washFlash silica gel column chromatography eluting with ethyl acetate-hexane=1-10 to 2-5 afforded ethyl 7-oxo-7-(1,3-thiazol-2-yl)heptanoate as a colorless oil (778 mg)

Sources & evidence

ORD record
ord-3b43489e85124f269410cae87e78d512
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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