Boron trifluoride etherate → Ethyl-1-propyl-1,3,4,9-tetrahydro-6-(phenylmethoxy)pyrano[3,4-b]indole-1-acetate

HRID 37701

반응식

HRID 37701 반응식
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]3[NH:15][CH:16]=[C:17]([CH2:18][CH2:19][OH:20])[C:11]=3[CH:10]=2)=[CH:3][CH:2]=1.[C:21]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])(=O)[CH2:22][CH2:23][CH3:24].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][C:21]1([CH2:22][CH2:23][CH3:24])[C:16]2[NH:15][C:12]3[C:11]([C:17]=2[CH2:18][CH2:19][O:20]1)=[CH:10][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[CH:14][CH:13]=3)[CH3:31]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 238498Ethyl 3-oxohexanoateHCID 7448495-Benzyloxy-3-(2-hydroxyethyl)indole

생성물 1

HCID 19935728Ethyl-1-propyl-1,3,4,9-tetrahydro-6-(phenylmethoxy)pyrano[3,4-b]indole-1-acetate수율 79.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 5-benzyloxytryptophol (4.72 g, 17 mmol) and ethyl butyrylacetate (3.16 g, 20 mmol) in methylene chloride (75 ml) is treated dropwise with boron trifluoride etherate (3 mL) and stirred under nitrogen at room temperature overnight. The reaction mixture is diluted with methylene chloride (250 mL) and sequentially washed with 5% aqueous sodium bicarbonate (2×100 mL) and water (2×50 mL). The organic phase is dried (MgSO4), filtered, and evaporated to afford 7.0 g of a crude dark oil. Purification by flash column chromatography (ethyl acetate:hexane, 1:9 eluent) on silica gel (50:1 ratio, 230-400 mesh) affords the title compound (5.5 g, 79%) as a slightly amber oil homogeneous by TLC.

후처리

  1. washsequentially washed with 5% aqueous sodium bicarbonate (2×100 mL) and water (2×50 mL)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford 7.0 g of a crude dark oil
  6. customPurification by flash column chromatography (ethyl acetate:hexane, 1:9 eluent) on silica gel (50:1 ratio, 230-400 mesh)

출처 및 근거

ORD 기록
ord-c478eada40d1417c9e940940bd675cfc
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420289

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