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

HRID 1385285Notes

Reaction equation

HRID 1385285 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([C:11]1[S:12][C:13](SC)=[C:14]2[C:19](=[O:20])[CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16][C:15]=12)#[N:10]>>[C:9]([C:11]1[S:12][C:13]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:14]2[C:19](=[O:20])[CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16][C:15]=12)#[N:10]

Participants

3

Reactant 2

HCID 27787536,6-Dimethyl-3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo(c)thiophene-1-carbonitrileHCID 178478990HCID 178478990, compound

Product 1

HCID 211844671-Cyano-3-cyclohexyl-6,6-dimethyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-oneYield 28%

Procedure

In the same way as described in Example 6, Step 1, using cyclohexylmagnesium chloride and 1-cyano-6,6-dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one, the title compound (0.63 g, 28%) was isolated as a cream solid. mp 129-132° C. 1HNMR (360 MHz, CDCl3) δ 1.07 (6H, s), 1.20-1.55 (5H, m), 1.75-1.85 (3H, m), 2.01-2.06 (2H, m), 2.42 (2H, s), 2.84 (2H, s), 3.85-3.94 (1H, M).

Sources & evidence

ORD record
ord-ff9770f8054946a3a0088ed824a8a777
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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