Citric Acid → HCID 19910765, compound

HRID 1607241Notes

Reaction equation

HRID 1607241 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:26]=[CH:25][C:11]([C:12]([C:14]2[O:15][C:16]3[CH:23]=[CH:22][CH:21]=[C:20](O)[C:17]=3[C:18]=2[CH3:19])=O)=[CH:10][CH:9]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:7][C:8]1[CH:26]=[CH:25][C:11]([C:12]([C:14]2[O:15][C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]=2[CH3:19])=[CH2:1])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 13849496HCID 13849496, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19910765HCID 19910765, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium t-butoxide (448 mg; 4mmoles) in tetrahydrofuran (25 mL) was added methyl-triphenylphosphonium bromide (1.07 gm; 3 mmoles). The mixture was stirred for a period o 2 hours. 2-(4-chlorobenzoyl)-3-methyl-4-hydroxybenzofuran (286 mg; 1mmole) in tetrahydrofuran (5 ml) was added rapidly and the mixture was stirred for an additional 30 minutes at room temperature. The mixture was poured into 10% citric acid solution (100 ml) and was extracted with ethylacetate. The organic phase was dried (Na2SO4), and concentrate in vacuo. The residue was chromatographed on silica gel and eluted with 10% ethylacetate in hexane to yield 210 mg (73%) of 2-(1-(4-chlorophenyl)vinyl)-3-methylbenzofuran as an oil.

Workup

  1. stirringthe mixture was stirred for an additional 30 minutes at room temperature
  2. extractionwas extracted with ethylacetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrate in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluted with 10% ethylacetate in hexane

Sources & evidence

ORD record
ord-559bdc8ba60949f585783a6ec92e9c33
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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