Water → HCID 18620104, compound

HRID 1862616Notes

Reaction equation

[CH2:1]([Li])CCC.[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]([CH:24]=[CH2:1])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (4.1 g) in tetrahydrofuran (40 ml) was added 1.56M n-butyl lithium solution in hexane (7.2 ml) at room temperature, and the mixture was stirred for 1 hour. After the reaction mixture was cooled to −70° C., a solution of methyl 2-benzyloxy-5-formylbenzoate (2.82 g) in tetrahydrofuran (40 ml) was added, and the resulting mixture was stirred for 15 hours with gradually warming up to room temperature. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1) gave methyl 2-benzyloxy-5-vinylbenzoate (2.63 g).

Workup

stirringthe resulting mixture was stirred for 15 hours
temperaturewith gradually warming up to room temperature
extractionthe resulting mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customAfter the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-b6921595418c415f9bb20f2b8a0e535e
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538152B1

Reaction notes

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