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Diethyl Ether → Methyl 2-benzyl-3-benzyloxy-3-[(4-morpholinyl)carbonyl]propionate

HRID 1535068
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HRID 1535068 반응식
[CH2:1]([O:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].CCOCC>C1COCC1.[Cl-].[Na+].O>[CH2:34]([CH:29]([CH:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:10]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[O:11])[C:30]([O:32][CH3:33])=[O:31])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10538169Methyl 2-bromo-3-phenylpropanoateHCID 19761610N-(Benzyloxyacetyl)morpholine

생성물 1

HCID 19761608Methyl 2-benzyl-3-benzyloxy-3-[(4-morpholinyl)carbonyl]propionate수율 63%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 57417360Sodium chloride; water용매

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온도
-78 °C

실험 절차

A -78° C. solution of N-(benzyloxyacetyl)morpholine (1 g, 8.5 mmol) in THF (25 mL) was treated with potassium bis(trimethylsilyl)amide (17 mL of a 0.5M solution). After stirring for 10 min at -78° C., a solution of methyl 2-bromo-3-phenylpropionate (8.5 mmol) in THF (5 mL) was added dropwise. Stirring at -78° C. for 30 min was followed by warming to 0° C. The reaction was then distributed between ether and brine solution. The organic layer was washed with brine and dried over MgSO4. Evaporation and flash chromatography on silica gel gave the desired product in 63% yield

후처리

  1. stirringStirring at -78° C. for 30 min
  2. temperatureby warming to 0° C
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customEvaporation and flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-43fdebd0839d4ce4aa090b037a50dd9a
출처 데이터셋
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05091575

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