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Triphenylphosphine → methyl 5-(acetylamino)-3,4-dihydro-2H-chromene-8-carboxylate

HRID 501519
Notes
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Reaction equation

HRID 501519 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7](O)[C:6]=1[CH2:16][CH2:17][CH2:18][OH:19])(=[O:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]2[C:6]=1[CH2:16][CH2:17][CH2:18][O:19]2)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 70859532HCID 70859532, compound

Product 1

HCID 54252685methyl 5-(acetylamino)-3,4-dihydro-2H-chromene-8-carboxylateYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 5A (1.80 g, 6.7 mmol) and Ph3P (1.94 g, 7.4 mmol) in THF (30 mL) cooled at 0° C. was added dropwise DEAD (1.17 mL, 7.4 mmol). After addition, the reaction mixture was stirred at rt for 2 h, then concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 50% to 100% EtOAc/hexane to furnish the title compound (1.3 g) as a white solid.

Workup

  1. additionAfter addition
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed (silica gel)
  4. washeluting with 50% to 100% EtOAc/hexane

Sources & evidence

ORD record
ord-b5780e669ba14a4babe93601a554e06b
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772267B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes