Sodium hydride → 2-(Diethoxyphosphoryl)-3-cyclopropylproprionic acid 4-methoxybenzyl ester

HRID 8777

반응식

HRID 8777 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:23]=[CH:22][C:8]([CH2:9][O:10][C:11](=[O:21])[CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1.Br[CH2:25][CH:26]1[CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11](=[O:21])[CH:12]([P:13]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20])=[O:14])[CH2:25][CH:26]2[CH2:28][CH2:27]2)=[CH:22][CH:23]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 540209272-(Diethoxyphosphoryl)acetic acid para-methoxybenzyl ester

생성물 1

HCID 540841052-(Diethoxyphosphoryl)-3-cyclopropylproprionic acid 4-methoxybenzyl ester수율 60.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of 60% sodium hydride in mineral oil (0.840 g, 21.0 mmol) in DMF (100 mL) was added a solution of 2-(diethoxyphosphoryl)acetic acid 4-methoxybenzyl ester (6.04 g, 19.1 mmol) from Step A in DMF (10 mL). The reaction mixture was stirred for 30 min at room temperature. Bromomethylcyclopropane (2.4 mL, 24.8 mmol) was added and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with diethyl ether, poured into saturated sodium bicarbonate, and extracted three times with diethyl ether. The organic layers were combined, washed with saturated sodium chloride, dried over sodium sulfate, and filtered. The volatiles were removed in vacuo and the residue was purified by FC (40% ethyl acetate in hexanes) to afford 4.31 g of the title compound.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 12 h
  2. extractionextracted three times with diethyl ether
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe volatiles were removed in vacuo
  7. customthe residue was purified by FC (40% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-e31142420d854a6b93bb0fdda233b4cb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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