Ethyl chloroformate → Diethyl 2-(4-(benzyloxy)phenyl)malonate

HRID 2268454

반응식

HRID 2268454 반응식
[Li+].CC([N-]C(C)C)C.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:29](Cl)(=[O:33])[O:30][CH2:31][CH3:32].[Cl-].[NH4+]>C1COCC1.CCCCCCC>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:29]([O:30][CH2:31][CH3:32])=[O:33])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27374284-Benzyloxyphenylacetic acid ethyl ester

생성물 1

HCID 2823246Diethyl 2-(4-(benzyloxy)phenyl)malonate수율 83.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8900Heptane용매

실험 절차

A heptane solution of LDA (2.0 M, 36.4 ml, 72.8 mmols) was dropwise added to a THF (130 ml) solution of ethyl 4-benzyloxyphenylacetate (13.1 g, 48.5 mmols) and ethyl chlorocarbonate (9.25 ml, 97.0 mmols), under a nitrogen stream at −70° C. or lower. The reaction mixture was stirred for 15 minutes, then a saturated aqueous ammonium chloride solution was added thereto, and the resulting mixture was allowed to warm to room temperature, and then extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting residue was washed with hexane to obtain the entitled compound (13.8 g) as crystals, which were further recrystallized from hexane.

후처리

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. customThe solvent was evaporated out in vacuo
  5. washthe resulting residue was washed with hexane

출처 및 근거

ORD 기록
ord-a66fbab7e4fc423199e0d459f2cedd78
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326369B1

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