Sodium Bicarbonate → HCID 20541499, compound

HRID 1065140Notes

Reaction equation

HRID 1065140 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2([O:12][Si](C)(C)C)[C:4]3([CH3:20])[CH:5]=[CH:6][CH:7]([CH2:19][CH:3]13)[C:8]2([CH3:18])[CH3:17].C([O-])(O)=O.[Na+].C(OCC)(=O)C.C(Cl)Cl>C(O)(=O)C.O1CCCC1.O>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2([OH:12])[C:4]3([CH3:20])[CH:5]=[CH:6][CH:7]([CH2:19][CH:3]13)[C:8]2([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 20541496HCID 20541496, compoundHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 20541499HCID 20541499, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of 21 mg of 1,2,3,4,4a,5,6,8a-octahydro-2oxo-4a-trimethylsilyloxy-5,5,8a-trimethyl-1,6-methanonaphthalene in 4 ml of acetic acid/tetrahydrofuran/water (3:1:1) was stirred under argon at 25° C. over 10 hours, then poured into saturated aqueous NaHCO3 solution and extracted with CH2Cl2. After chromatography (SiO2, ethyl acetate/CH2Cl2) and sublimation, there were obtained 15 mg of 1,2,3,4,4a,5,6,8a-octahydro-2-oxo-4a-hydroxy-5,5,8a-trimethyl-1,6-methanonaphthalene (m.p. 112°-115° C., 95% yield).

Workup

  1. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-502da933354b4732a7731befd6dd7b5f
Source dataset
uspto-grants-1982_05
Patent number
US04328352

Reaction notes

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