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Boron trifluoride etherate → 1-Ethyl-1,3,4,9-tetrahydro-6-(phenylmethoxy)pyrano[3,4-b]indole-1-acetic acid methyl ester

HRID 484247
Notes
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Reaction equation

HRID 484247 reaction equation
[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.CO[C:23]([CH2:29][CH3:30])=[CH:24][C:25]([O:27][CH3:28])=[O:26].B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:28][O:27][C:25](=[O:26])[CH2:24][C:23]1([CH2:29][CH3:30])[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 7448495-Benzyloxy-3-(2-hydroxyethyl)indoleHCID 1501841Methyl 3-methoxypent-2-enoate

Product 1

HCID 543507501-Ethyl-1,3,4,9-tetrahydro-6-(phenylmethoxy)pyrano[3,4-b]indole-1-acetic acid methyl esterYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

A mixture consisting of 5-benzyloxytryptophol (24.0 g, 0.090 mol), methylene chloride (600 mL), methyl 3-methoxy-2-pentenoate (16.8 g, 0.177 mol) and borontrifluoride etherate (2 mL) is stirred at room temperature for 3 hours. The reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL), dried (MgSO4), filtered and concentrated to give 38.0 g crude product. The crude product is flash chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent to afford 29.0 g pure title compound, m.p. 98°-100° C.

Workup

  1. washThe reaction mixture is washed with 5% NaHCO3 (2×200 mL), water (2×200 mL) and once with brine (200 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give 38.0 g crude product
  6. customchromatographed on silica gel using 20% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record
ord-7e1497e3b270441998354f2219934c08
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05229516

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes