Methanol → 6-Ethynyl-1-(iso-propyl-methyl-amino)-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene

HRID 844651Notes

Reaction equation

HRID 844651 reaction equation
[CH3:1][N:2]([CH:21]([CH3:23])[CH3:22])[CH:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]#[C:14][Si](C)(C)C)=[CH:10][CH:11]=2)[C:6]([CH3:20])([CH3:19])[CH2:5][CH2:4]1.CO.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[C:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[CH:3]([N:2]([CH:21]([CH3:22])[CH3:23])[CH3:1])[CH2:4][CH2:5][C:6]2([CH3:19])[CH3:20])#[CH:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 225688201-(Methyl-iso-propylamino)-4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene2×

Product 1

HCID 225689626-Ethynyl-1-(iso-propyl-methyl-amino)-4,4-dimethyl-1,2,3,4-tetrahydronaphthaleneYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure E and using 1-(methyl-iso-propylamino)-4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene (Intermediate 28, 0.14 g, 0.45 mmol), methanol (5 mL), potassium carbonate (0.61 g, 4.41 mmol) and ethyl acetate the title compound (0.092 g, 80%) was obtained as an oil.

Sources & evidence

ORD record
ord-c3d5fc5f40ed4f95ab4d0d0611d57d5a
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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