(4-Carboxybutyl)triphenylphosphonium bromide → 6-(1,4-Dimethoxy-3-methylnaphthalen-2-yl)hex-5-enoic acid

HRID 2393183Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH:16]=O.[Br-].[C:19]([CH2:22][CH2:23][CH2:24][CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:21])=[O:20].CC(C)([O-])C.[K+]>CC(O)(C)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH:16]=[CH:25][CH2:24][CH2:23][CH2:22][C:19]([OH:21])=[O:20]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 1 g of 1,4-dimethoxy-3-methylnaphthalene-2-carbaldehyde and 3.85 g of (4-carboxybutyl)triphenylphosphonium bromide in 2.5% t-BuOH/toluene at 60° C. was added 1.95 g of potassium t-butoxide. The mixture was stirred at 60° C. for 30 min, extracted with 1N NaOH, and washed with toluene. The aqueous layer was neutralized with iN HCl until pH 4-5, then extracted with ethyl acetate. The organic layer was washed, dried, and concentrated, then the trsidue was purified with column chromatography over silica gel using n-hexane/ethyl acetate (2/1) as an eluent to give 0.9 g of the titled compound as an oil.

Workup

extractionextracted with 1N NaOH
washwashed with toluene
extractionextracted with ethyl acetate
washThe organic layer was washed
customdried
concentrationconcentrated
customthe trsidue was purified with column chromatography over silica gel

Sources & evidence

ORD record: ord-866a80352ea74365bab01d08ccdb5c2f
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05804601

Reaction notes

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