Sodium hydride → HCID 23150318, 화합물

HRID 657653

반응식

HRID 657653 반응식
[H-].[Na+].[Cl-].[CH2:4]([O:11][C:12]1[CH:37]=[CH:36][C:15]([CH2:16][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[O:38]1[C:42]2([CH2:47][CH2:46][C:45](=O)[CH2:44][CH2:43]2)[O:41][CH2:40][CH2:39]1>CN(C)C=O.CCCCC>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH:16]=[C:45]2[CH2:46][CH2:47][C:42]3([O:41][CH2:40][CH2:39][O:38]3)[CH2:43][CH2:44]2)=[CH:36][CH:37]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 383834[4-(Benzyloxy)benzyl](triphenyl)phosphonium chlorideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

생성물 1

HCID 23150318HCID 23150318, 화합물수율 47.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8003Pentane용매

실험 절차

To a suspension of sodium hydride (729 mg 60% in mineral oil) in N,N-dimethylformamide containing one drop of pentane is added (4-benzyloxybenzyl)triphenylphosphonium chloride (7.52 g). The mixture is stirred for 40 min, then 1,4-dioxaspiro[4.5]decan-8-one (2.37 g) is added. The mixture is stirred for one hour at room temperature, the suspension turning from red to green. The mixture is poured into ice (250 g) and extracted with ethyl acetate (4 times 100 mL). The organic extracts are pooled, washed with saturated aqueous solution of sodium chloride (3 times 50 mL), dried over magnesium sulfate, concentrated under reduced pressure and purified by column chromatography over silica gel using a gradient heptane/ethyl acetate from 90/10 to 60/40 to give 2.43 g of 8-(4-benzyloxybenzylidene)-1,4-dioxaspiro[4.5]decane as a colorless oil.

후처리

  1. stirringThe mixture is stirred for one hour at room temperature
  2. extractionextracted with ethyl acetate (4 times 100 mL)
  3. washwashed with saturated aqueous solution of sodium chloride (3 times 50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography over silica gel using a gradient heptane/ethyl acetate from 90/10 to 60/40

출처 및 근거

ORD 기록
ord-a0d55fc031b34fdaa2f393175b7338b6
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076329B2

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