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

HRID 354573

反応式

HRID 354573 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-70e71b7d612e41a19000ff3c86dc976e
出典データセット
uspto-grants-1983_03
特許番号
US04375475

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