Sodium Bicarbonate → 2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one

HRID 486870Notes

Reaction equation

HRID 486870 reaction equation
[OH:1][C:2]1(C#N)[CH2:15][C:14]([CH3:16])=[CH:13][CH2:12][CH2:11][C:10]([CH3:17])=[CH:9][CH2:8][CH2:7][C:6]([CH3:18])=[CH:5][CH:4]=[C:3]1[CH:19]([CH3:21])[CH3:20].C(=O)([O-])O.[Na+]>C(OCC)C>[CH3:21][CH:19]([C:3]1[C:2](=[O:1])[CH2:15][C:14]([CH3:16])=[CH:13][CH2:12][CH2:11][C:10]([CH3:17])=[CH:9][CH2:8][CH2:7][C:6]([CH3:18])=[CH:5][CH:4]=1)[CH3:20]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 54189898HCID 54189898, compound

Product 1

HCID 570081642-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-oneYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the cyanohydrin which is 1-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraenecarbonitrile (78.0 mg, 0.25 mmol) in ethyl ether (4 ml) is added to a saturated aqueous sodium hydrogen carbonate solution (2 ml) on an ice-water bath and the mixture is stirred for 10 minutes under nitrogen atmosphere. After confirming disappearance of the starting compound, the organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting residue is subjected to silica gel column chromatography (eluent: n-hexane/ethyl acetate=7:1) to give the desired ketone, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene -1-on (58.0 mg, 75%).

Workup

  1. washthe organic layer is washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-021362fedcf24695b6369495caa2bcaf
Source dataset
uspto-grants-1994_03
Patent number
US05292911

Reaction notes

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