Triethyloxonium tetrafluoroborate → HCID 86738080, compound

HRID 848814Notes

Reaction equation

HRID 848814 reaction equation
O[CH:2]([CH3:27])[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:28][B-:29]([F:32])([F:31])[F:30].C([O+](CC)CC)C>C(Cl)Cl.C(=O)=O.CC(C)=O>[F:28][B-:29]([F:32])([F:31])[F:30].[C:8]1([P+:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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]([CH3:27])[O:26]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 178467854HCID 178467854, compound

Product 1

HCID 86738080HCID 86738080, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 18522661Acetone cardiceSolvent

Procedure

1.5 g of (5-hydroxy-2-oxohexyl)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, and solvent removed to afford the desired product, m.p. 118.5°-122° C. and having the formula ##STR8##

Workup

  1. customdecanted into ice water
  2. stirringstirred vigorously with the addition of an additional 30 ml of methylene chloride
  3. extractionThe extraction
  4. customsolvent removed

Sources & evidence

ORD record
ord-d36f607f297247f2acc9373006addf8c
Source dataset
uspto-grants-1981_10
Patent number
US04297487

Reaction notes

Loading…