Sodium Hydroxide → HCID 22660710, compound

HRID 392796Notes

Reaction equation

HRID 392796 reaction equation
[CH2:1]=[C:2]1[CH2:15][CH2:14][C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][O:6]2)[CH2:4][C:3]1=O.CSC.B.[OH-:21].[Na+].[O-:23]O>O1CCCC1.O>[OH:21][CH2:1][CH:2]1[CH2:15][CH2:14][C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:23])[O:6]2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 18500Perhydroxyl radicalHCID 12423031(Dimethyl sulfide)trihydroboronHCID 22660678HCID 22660678, compound

Product 1

HCID 22660710HCID 22660710, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methylenespiro[cyclohexane-1,1′(3′H)-isobenzofuran]-3-one (196 mg) in anhydrous tetrahydrofuran (5.0 mL) was cooled to 0° C., to which borane-dimethyl sulfide complex (2M tetrahydrofuran solution, 690 μL) was added and the mixture was stirred at that temperature for 1.5 hours, then additional 20 minutes together with aqueous 2M sodium hydroxide (5.0 mL) and aqueous 30% hydroperoxide (5.0 mL). The reaction mixture was diluted with water, extracted with ethyl acetate, washed with saturated saline solution, then dried over anhydrous Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give the subject compound (190 mg) as diastereomers.

Workup

  1. additionwas added
  2. customadditional 20 minutes
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated saline solution
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-000c6e25b54e4beaa7fe5cf889a6b9fc
Source dataset
uspto-grants-2004_10
Patent number
US06803372B2

Reaction notes

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