Water → HCID 53926625, compound

HRID 1111191Notes

Reaction equation

HRID 1111191 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])[CH2:8]CC.[C:12]([O:15][C:16]1[C:17]([CH3:30])=[C:18]([CH3:29])[C:19]2[O:23][C:22]([CH:25]=[O:26])([CH3:24])[CH2:21][C:20]=2[C:27]=1[CH3:28])(=[O:14])[CH3:13].O>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:12]([O:15][C:16]1[C:17]([CH3:30])=[C:18]([CH3:29])[C:19]2[O:23][C:22]([C:25](=[O:26])[CH:1]=[CH:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)([CH3:24])[CH2:21][C:20]=2[C:27]=1[CH3:28])(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 15086717HCID 15086717, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 53926625HCID 53926625, compound

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of benzyltriphenyl phosphonium chloride [1.5 g (3.87 mmol)] in tetrahydrofuran (5 ml) was added dropwise, under ice-cooling, an n-butyl lithium hexane solution [(1.6M) 24 ml], followed by stirring for 15 minutes. To the reaction mixture was added a solution of 5-acetoxy-2-formyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (1.0 g) in tetrahydrofuran (3 ml). To the mixture was added water and it was subjected to extraction with ethyl acetate. The extract solution was washed with water and dried, then the solvent was distilled off. The residue was purified by means of a silica gel column chromatography [hexane-IPE(2:1)] to obtain the desired 5-acetoxy-2-cinnamoyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (Compound 11) (1.22 g).

Workup

  1. additionwas added dropwise, under ice-
  2. temperaturecooling
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe extract solution was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by means of a silica gel column chromatography [hexane-IPE(2

Sources & evidence

ORD record
ord-679e1e9ae76a4c8fb4def3b56c26b77c
Source dataset
uspto-grants-1990_12
Patent number
US04978761

Reaction notes

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