Benzaldehyde, 4-(phenylmethoxy)- → HCID 67405487, compound

HRID 1909545Notes

Reaction equation

HRID 1909545 reaction equation
[Cl-].[F:2][C:3]1[CH:4]=[C:5]([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][C:7]=2[CH:13]=1.C([Li])CCC.[CH2:39]([O:46][C:47]1[CH:54]=[CH:53][C:50]([CH:51]=O)=[CH:49][CH:48]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1>[CH2:39]([O:46][C:47]1[CH:48]=[CH:49][C:50]([CH:51]=[CH:14][C:5]2[C:6]3[O:10][C:9]([CH3:11])([CH3:12])[CH2:8][C:7]=3[CH:13]=[C:3]([F:2])[CH:4]=2)=[CH:53][CH:54]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 86643715HCID 86643715, compoundHCID 178418339Butyllithium

Product 1

HCID 67405487HCID 67405487, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ((5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methyl)triphenyl phosphonium chloride (648) (500 mg, 1.09 mmol) in anhydrous tetrahydrofuran at room temperature (10 mL) was added n-butyllithium (0.67 mL, 1.31 mmol, 2 M in hexane). After stirring for 10 min 4-(benzyloxy)benzaldehyde (231 mg, 1.09 mmol) was added and stirred for an additional 3 hours. The reaction was quenched with water and extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (20%) to give 7-(4-(benzyloxy)styryl)-5-fluoro-2,2-dimethyl-2,3-dihydrobenzofuran as a cis/trans mixture (649).

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (20%)

Sources & evidence

ORD record
ord-c3a6a7ee7200419a9939767700f5c3f8
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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