Tetrahydrofuran → HCID 19736369, compound

HRID 326218Notes

Reaction equation

HRID 326218 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([CH3:8])[C:4]([CH3:10])([CH3:9])[C:3]=1[CH2:11][CH2:12][C:13](=[O:15])[CH3:14].[OH-].[K+].[NH4+].[Cl-].[CH2:20]1C[O:23][CH2:22][CH2:21]1>O>[CH3:14][C:13]([OH:15])([CH2:12][CH2:11][C:3]1[C:4]([CH3:9])([CH3:10])[CH:5]([CH3:8])[CH2:6][CH2:7][C:2]=1[CH3:1])[C:20]#[C:21][CH2:22][OH:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 144893214-(2,5,6,6-Tetramethylcyclohex-1-en-1-yl)butan-2-one

Product 1

HCID 19736369HCID 19736369, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-2-butanone (13 g, 0.061 mol) and propargylic alcohol (4 g, 0.071 mol) was added within 100 min to a mechanically stirred slurry of powdered KOH (26 g, 0.46 mol) in THF (100 ml) at 20° C. under N2. After 3 h at 20°, the brown mixture was poured into a cold solution of NH4Cl (28 g) in H2O (100 ml). Extraction with ether, workup and chromatography [SiO2, (200 g), cyclohexane/ethyl acetate 7:3] afforded 4-methyl-6-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-2-hexyn-1,4-diol as a viscous pale-yellow oil (12.3 g, 77%).

Workup

  1. extractionExtraction with ether, workup and chromatography [SiO2, (200 g), cyclohexane/ethyl acetate 7:3]

Sources & evidence

ORD record
ord-77157b0d37bc4956b00592ad832d86c3
Source dataset
uspto-grants-1993_12
Patent number
US05268355

Reaction notes

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