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

HRID 8777

反応式

HRID 8777 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e31142420d854a6b93bb0fdda233b4cb
出典データセット
uspto-grants-2006_08
特許番号
US07091211B2

関連ノート

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