Methanol → 1,3-Di-tert-butyl-5-ethynyl-2-methoxy-benzene

HRID 1861516Notes

Reaction equation

HRID 1861516 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:17]#[C:18][Si](C)(C)C)[CH:8]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CO>CCCCCC>[C:13]([C:9]1[CH:8]=[C:7]([C:17]#[CH:18])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[O:11][CH3:12])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 22568920(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-trimethyl-silane2×

Product 1

HCID 225688511,3-Di-tert-butyl-5-ethynyl-2-methoxy-benzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following General Procedure E and (3,5-di-tert-butyl-4-methoxy-phenylethynyl)-trimethyl-silane (Intermediate 168, 0.28 g, 0.9 mmol), potassium carbonate (0.98 g, 7.1 mmol) and methanol (10 mL) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as the eluent, the title compound was obtained (0.23 g, 100%).

Sources & evidence

ORD record
ord-6bc11223be814cb186ccfd6f6f143c08
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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