6,6-Dimethyl-3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo(c)thiophene-1-carbonitrile → 1-Cyano-3-cyclobutyl-6,6-dimethyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one

HRID 1385286Notes

Reaction equation

HRID 1385286 reaction equation
[CH:1]1([Mg]Br)[CH2:4][CH2:3][CH2:2]1.[C:7]([C:9]1[S:10][C:11](SC)=[C:12]2[C:17](=[O:18])[CH2:16][C:15]([CH3:20])([CH3:19])[CH2:14][C:13]=12)#[N:8]>>[C:7]([C:9]1[S:10][C:11]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[C:12]2[C:17](=[O:18])[CH2:16][C:15]([CH3:20])([CH3:19])[CH2:14][C:13]=12)#[N:8]

Participants

3

Reactant 2

HCID 27787536,6-Dimethyl-3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo(c)thiophene-1-carbonitrileHCID 178419648HCID 178419648, compound

Product 1

HCID 211844941-Cyano-3-cyclobutyl-6,6-dimethyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-oneYield 18%

Procedure

In the same way as described in Example 6, Step 1, using cyclobutylmagnesium bromide and 1-cyano-6,6-dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one, the title compound (0.37 g, 18%) was isolated as a pale yellow solid. mp 65-68° C. 1HNMR (360 MHz, CDCl3) δ 1.06 (6H, s), 1.90-1.98 (1H, m), 2.00-2.12 (3H, m), 2.40 (2H, s), 2.50-2.62 (2H, m), 2.83 (2H, s), 4.45-4.56 (1H, m).

Sources & evidence

ORD record
ord-67d5c759f1c64da9b2c11fd7facd0478
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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