Triethyloxonium tetrafluoroborate → HCID 86738080, compound

HRID 223631Notes

Reaction equation

HRID 223631 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5](=[O:26])[CH2:6][PH:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:27][B-:28]([F:31])([F:30])[F:29].[CH2:32]([O+](CC)CC)C>C(Cl)Cl.C(=O)=O.CC(C)=O>[F:27][B-:28]([F:31])([F:30])[F:29].[C:8]1([P+:7]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[C:5]2[CH2:4][CH2:3][CH:2]([CH3:32])[O:26]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 178520687HCID 178520687, compound

Product 1

HCID 86738080HCID 86738080, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 18522661Acetone cardiceSolvent

Conditions

Temperature
-78 °C

Procedure

1.5 g of (5-hydroxy-2-oxopentyl)triphenylphosphorane was dissolved in 20 ml of methylene chloride under a nitrogen atmosphere, cooled in dry ice/acetone bath and 15 ml of triethyloxonium tetrafluoroborate as a 1 M solution in methylene chloride was added. The reaction mixture was stirred at about -78° C. for 0.5 hour and allowed to warm to room temperature over about 2 hours, decanted into ice water and stirred vigorously with the addition of an additional 30 ml of methylene chloride. The extraction was repeated twice, the extracts combined, dried over sodium sulfate, the solvent removed under nitrogen gas followed by warming to 40° C. for 2 hours at 0.5 mm. Crystallization from ethyl acetate gave 700 mg of the desired product, m.p. 118.5°-122.5° C.

Workup

  1. temperatureto warm to room temperature over about 2 hours
  2. customdecanted into ice water
  3. stirringstirred vigorously with the addition of an additional 30 ml of methylene chloride
  4. extractionThe extraction
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed under nitrogen gas
  7. temperatureby warming to 40° C. for 2 hours at 0.5 mm
  8. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-31f0ba4fe6b74e34b1d8e1088e2c5a89
Source dataset
uspto-grants-1982_10
Patent number
US04355182

Reaction notes

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