Water → HCID 13044957, compound

HRID 615552Notes

Reaction equation

HRID 615552 reaction equation
[F:1][CH:2]([C:21]1[O:22]CC(C)(C)N=1)[CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(Cl)(Cl)Cl.[OH2:32]>Cl>[F:1][CH:2]([CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:21]([OH:22])=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 6212ChloroformHCID 54302151HCID 54302151, compound

Product 1

HCID 13044957HCID 13044957, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
23 °C

Procedure

A suspension of 2-(1-fluorononadec-13-en-4,7-diynyl)-4,5-dihydro-4,4-dimethyloxazole (86 mg) in 3 ml of 3N HCl was refluxed with stirring under argon for 15 min. It was cooled to about 23° C., diluted with 3 ml of water, and extracted three times with ether. The ether extracts were combined, washed with brine, and dried over MgSO4. Concentration of ether at 35° C./35 mmHg gave the crude acid which was purified by flash chromatography on silica gel (8 g, 230-400 mesh). Elution with HOAc--CH3OH--CHCl3 under nitrogen afforded 49 mg (66% yield by weight) of (Z)-2-fluoro-14-eicosene-5,8-diynoic acid as a colorless oil.

Workup

  1. temperaturewas refluxed
  2. extractionextracted three times with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customConcentration of ether at 35° C./35 mmHg gave the crude acid which
  6. customwas purified by flash chromatography on silica gel (8 g, 230-400 mesh)
  7. washElution with HOAc--CH3OH

Sources & evidence

ORD record
ord-5bd56a6feac8474da1c3ed9a1be3fe87
Source dataset
uspto-grants-1985_02
Patent number
US04500462

Reaction notes

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