Methanol → 8-Ethyl-6-ethynyl-2,2,4,4-tetramethylchroman

HRID 841620Notes

Reaction equation

HRID 841620 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:17]#[C:18][Si](C)(C)C)[CH:6]=[C:7]2[C:12]=1[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]2([CH3:16])[CH3:15])[CH3:2].CO.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CCCCCC>[CH2:1]([C:3]1[CH:4]=[C:5]([C:17]#[CH:18])[CH:6]=[C:7]2[C:12]=1[O:11][C:10]([CH3:13])([CH3:14])[CH2:9][C:8]2([CH3:16])[CH3:15])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 695486138-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman2×

Product 1

HCID 225690198-Ethyl-6-ethynyl-2,2,4,4-tetramethylchroman

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following general procedure E and using 8-ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman (Intermediate 47, 0.137 g, 0.44 mmol), methanol and potassium carbonate (0.1 g, 0.72 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.066 g, 62%).

Sources & evidence

ORD record
ord-55cd15b95922435f99d10bb2c8206913
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

Loading…