Hydrogen Peroxide → HCID 14699195, compound

HRID 1200135Notes

Reaction equation

HRID 1200135 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH2:4][C:5](=[O:35])[CH2:6][CH:7]([OH:34])/[CH:8]=[CH:9]/[C:10]1[C:11]2([CH2:16][C:17]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:18][C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:15][CH2:14][CH2:13][CH2:12]2.C(B(CC)CC)C.[BH4-].[Na+].OO>C1COCC1.O.C(OCC)(=O)C.CO>[CH3:1][O:2][C:3](=[O:36])[CH2:4][CH:5]([OH:35])[CH2:6][CH:7]([OH:34])/[CH:8]=[CH:9]/[C:10]1[C:11]2([CH2:16][C:17]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:18][C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15]2

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 7357TriethylboraneHCID 4311764Sodium borohydrideHCID 14699194HCID 14699194, compound

Product 1

HCID 14699195HCID 14699195, compoundYield 93%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl-(E)-7-[7,9-di-(4-fluorophenyl)spiro-[4.5]deca-6,8-dien-6-yl]-5-hydroxy-3-oxo-6-heptenoate (3.0 g, 6.09 mmoles) in 80 ml of anhydrous THF was added a 1M THF solution of triethylborane (9.07 ml, 9.07 mmoles). The solution was stirred for 5 minutes at room temperature and was then cooled to -78° C. in a dry ice-acetone bath. To this mixture was added sodium borohydride (0.27 g, 7.0 mmoles) followed by the dropwise addition over 30 minutes of a solution of 6.09 ml of methanol in 15 ml of THF. The reaction was stirred for 1 hour with the temperature slowly rising to -50° C. To this mixture was added a solution of 30% hydrogen peroxide (14.17 ml) in water (7 ml) dropwise over 5 minutes. The reaction was stirred at room temperature for 1 hour and was poured into 200 ml of ethyl acetate. The mixture was extracted with 1N HCl and then brine. The organic layer was evaporated in vacuo to give 2.8 g of material. The residue was dissolved in ethyl acetate and the solution was diluted with hexane to precipitate a solid product having an m.p. of 113°-15° C. (dec).

Workup

  1. temperaturewas then cooled to -78° C. in a dry ice-acetone bath
  2. stirringThe reaction was stirred for 1 hour with the temperature
  3. customslowly rising to -50° C
  4. stirringThe reaction was stirred at room temperature for 1 hour
  5. extractionThe mixture was extracted with 1N HCl
  6. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-5d1298a41a7545d2926346298089aedf
Source dataset
uspto-grants-1990_02
Patent number
US04904691

Reaction notes

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