Ethanol → HCID 53927856, compound

HRID 1579079Notes

Reaction equation

[CH3:1][C:2]([CH:8]=[CH:9][CH2:10][CH:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:3][C:4](=[O:7])[CH2:5][CH3:6].[OH-].[K+].[BH4-].[Na+].[CH2:23]([OH:25])[CH3:24]>>[CH2:23]([O:25][C:15]([CH3:16])([CH3:17])[CH2:14][CH2:13][CH2:12][CH:11]([CH3:18])[CH2:10][CH:9]=[CH:8][C:2]([CH3:1])=[CH:3][C:4](=[O:7])[CH2:5][CH3:6])[CH3:24]

Participants

Reactant 4

HCID 702Ethanol3×

HCID 14797Potassium Hydroxide

HCID 4311764Sodium borohydride

HCID 54521383HCID 54521383, compound

Product 1

HCID 53927856HCID 53927856, compound

Procedure

To a solution of 2 g. of 5,9,13-trimethyltetradeca-4,6,12-trien-3-one in 20 ml. of ethanol, cooled to 0° by an ice-bath, is added a suspension of 2.32 g. of mercuric acetate in 50 ml. of ethanol over 15 minutes. The reaction mixture is stirred for 2 hours and then with cooling, to -20°, 1.22 g. of potassium hydroxide in 20 ml. of ethanol is added. Then 0.139 g. of sodium borohydride is added in small portions and stirring continued for 30 minutes at -20°. The solution is decanted, then concentrated to half volume, diluted with 100 ml. of water and extracted with ether (3 × 50). The ethereal phase is washed with water, dried over magnesium sulfate and the crude product chromatographed on silica to yield 13-ethoxy-5,9,13-trimethyltetradeca-4,6-dien-3-one.

Workup

additionis added
additiona suspension of 2.32 g
temperaturewith cooling, to -20°
stirringstirring
waitcontinued for 30 minutes at -20°
customThe solution is decanted
concentrationconcentrated to half volume
additiondiluted with 100 ml
extractionof water and extracted with ether (3 × 50)
washThe ethereal phase is washed with water
dry with materialdried over magnesium sulfate
customthe crude product chromatographed on silica

Sources & evidence

ORD record: ord-3c51cab74b824415a9e71450af5438fb
Source dataset: uspto-grants-1976_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03940444

Reaction notes

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