Hydrochloric Acid → HCID 66874614, compound

HRID 1799634Notes

Reaction equation

HRID 1799634 reaction equation
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1.Cl>O1CCCC1.O>[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:4]([OH:6])=[O:5])=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 10918084Phosphonium, (8-carboxyoctyl)triphenyl-, bromide

Product 1

HCID 66874614HCID 66874614, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 0.65 g, 16 mmol) was added portionwise at room temperature to a stirred solution of (8-carboxy-octyl)-triphenyl-phosphonium bromide (2.8 g, 5.6 mmol) in tetrahydrofuran (30 mL) at room temperature, then after 1 hour 4-fluorobenzaldehyde (700 mg, 5.64 mmol) was added portionwise to the reaction mixture and the solution stirred for 2 days at room temperature. On reaction completion, water (10 ml) was added and the solution acidified to pH 3 with concentrated hydrochloric acid. The product was extracted with ethyl acetate, the organic layer dried over magnesium sulfate, filtered and evaporated. Chromatography (SiO2, heptane-ethyl acetate 4:1) afforded 10-(4-fluoro-phenyl)-dec-9-enoic acid (280 mg, 19%) as a colorless oil.

Workup

  1. additionwas added
  2. extractionThe product was extracted with ethyl acetate
  3. dry with materialthe organic layer dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3b555ebeff164425a7d18e0383631ef6
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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