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Triethylamine → alpha-(o-Fluorobenzoylthiomethyl)-beta-phenyl-gamma-butyrolactone

HRID 65262
Notes
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Reaction equation

HRID 65262 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[SH:11][CH2:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][O:16][C:14]1=[O:15].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)C>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([S:11][CH2:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][O:16][C:14]1=[O:15])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99352-Fluorobenzoic acidHCID 199401P,P-Diphenylphosphinic azideHCID 13518975alpha-Mercaptomethyl-beta-phenyl-gamma-butyrolactone

Product 1

HCID 13518918alpha-(o-Fluorobenzoylthiomethyl)-beta-phenyl-gamma-butyrolactoneYield 67.2%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.2 g of o-fluorobenzoic acid and 1.5 g of α-mercaptomethyl-β-phenyl-γ-butyrolactone in 20 ml of dimethylformamide were added 1.9 ml of diphenylphosphoryl azide (DPPA) and then 1.2 ml of triethylamine under ice-cooling. Then, the mixture was raised to a room temperature and stirred for 18 hours. After completion of the reaciton, the reaction mixture was diluted with 200 ml of ethyl ether, washed with 5% hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated saline, dried over magnesium sulfate and the solvent was then distilled off. The crude product thus obtained was purified by a silica gel column chromatography to give 1.6 g (yield 67%) of the title compound.

Workup

  1. washwashed with 5% hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated saline
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. customThe crude product thus obtained
  5. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-0a89f202a1ce4947b408e89c52abab67
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04613613

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes