Ethyl bromoacetate → Ethyl 5-Acetoxy-7-(2,4-dichlorophenyl)-3-hydroxy-3-methyl-6-heptenoate

HRID 354573

반응식

HRID 354573 반응식
[C:1]([O:4][CH:5]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:6][C:7](=[O:9])[CH3:8])(=[O:3])[CH3:2].BrC[C:22]([O:24][CH2:25][CH3:26])=[O:23].[Cl-].[CH2:28]([Al+]CC)C>C1COCC1.[Zn]>[C:1]([O:4][CH:5]([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:6][C:7]([OH:9])([CH3:28])[CH2:8][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 7748Ethyl bromoacetateHCID 16686102Diethyl aluminum chlorideHCID 544676676-(2,4-Dichlorophenyl)-2-oxo-5-hexene-4-yl Acetate

생성물 1

HCID 54268776Ethyl 5-Acetoxy-7-(2,4-dichlorophenyl)-3-hydroxy-3-methyl-6-heptenoate수율 73.4%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 6-(2,4-dichlorophenyl)-2-oxo-5-hexene-4-yl acetate (1.3 g, 4.3 mmole) and ethyl bromoacetate (0.47 ml, 4.2 mmole) in dry THF (10 ml) was added dropwise to a vigorously stirred slurry of activated zinc dust (490 mg, 7.5 mmole), cuprous bromide (29 mg, 0.2 mmole), diethylaluminum chloride (25% solution in toluene; 1.72 ml, 4.3 mmole) and dry THF (5 ml) under N2 at 20° C. Stirring was continued for 5 hours before quenching with pyridine (3.5 ml). After the addition of water (50 ml) the mixture was extracted with ether (3×80 ml). The combined ether extracts were washed with 1 N HCl (2×25 ml), H2O (2×50 ml) and brine, then dried (MgSO4), filtered and evaporated leaving the crude title compound as a pale yellow oil (1.2 g); pmr (CDCl3) δ1.28 (3 H, t), 1.33 (3H, t), 2.10 (3H, s).

후처리

  1. custombefore quenching with pyridine (3.5 ml)
  2. additionAfter the addition of water (50 ml) the mixture
  3. extractionwas extracted with ether (3×80 ml)
  4. washThe combined ether extracts were washed with 1 N HCl (2×25 ml), H2O (2×50 ml) and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-70e71b7d612e41a19000ff3c86dc976e
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04375475

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