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Ethyl Acetate → 4-[2-(4-Bromo-phenyl)-2-methoxycarbonyl-ethyl]-benzoic acid tert-butyl ester

HRID 1401891
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인쇄 미리보기

반응식

HRID 1401891 반응식
C(O[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1C)(=O)C.[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25]I)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:38]([O:41][CH2:42]C)(=[O:40])[CH3:39]>C1COCC1.O>[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:39]([C:5]2[CH:6]=[CH:7][C:8]([Br:11])=[CH:9][CH:10]=2)[C:38]([O:41][CH3:42])=[O:40])=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 2733832Lithium hexamethyldisilazaneHCID 600267744-Bromo-2-methylphenyl acetateHCID 672121184-Iodomethyl benzoic acid tert-butyl ester

생성물 1

HCID 672113474-[2-(4-Bromo-phenyl)-2-methoxycarbonyl-ethyl]-benzoic acid tert-butyl ester수율 100%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 246.63 g of methyl-4-bromophenyl acetate and 342.54 g of 4-Iodomethyl benzoic acid tert-butyl ester in THF (1233 mL) was cooled to −8° C. A solution of lithium hexamethyl disilazide in THF (1185 mL, 1.0 M) was added dropwise ensuring that the temperature remaine below −2° C. After the addition was complete, the reaction was allowed to proceed for ˜45 min at the same temperature and then poured over a stirring mixture of ethyl acetate (2.46 L) and water (1.23 L). The organic phase was washed with saturated ammonium chloride and then with water. Dried over magnesium sulfate and concentrated under reduced pressure to obtain 450.5 g (100% yield) thick oil. HNMR: CDCl3, 1.41 (s, 9H), 2.88-2.90 (m, 1H), 3.24-3.28 (m, 1H), 3.45 (s, 3H), 3.63 (t, 1H). 6.96-6.99 (m, 4H), 7.25 (d, 2H), 7.68 (d, 2H)

후처리

  1. customremaine below −2° C
  2. additionAfter the addition
  3. washThe organic phase was washed with saturated ammonium chloride
  4. dry with materialDried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6d779bdda11245fc89438c93af105045
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08907103B2

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