Sodium hydride → HCID 54021354, compound

HRID 1954300Notes

Reaction equation

HRID 1954300 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([OH:23])=[C:17]([CH2:24][CH3:25])[CH:16]=4)[C:4]=2[C:3]=1[CH3:26])[CH:12]=[CH:11][CH:10]=[CH:9]3.[H-].[Na+].[CH3:29][O:30][C:31]1[C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][S:33][C:32]=1[S:40](Cl)(=[O:42])=[O:41]>>[CH3:39][O:38][C:36]([C:35]1[C:31]([O:30][CH3:29])=[C:32]([S:40]([O:23][C:18]2[C:19]([CH2:21][CH3:22])=[CH:20][C:15]([C:14]3[C:4]4[C:3]([CH3:26])=[C:2]([CH3:1])[S:6][C:5]=4[CH:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[CH:16][C:17]=2[CH2:24][CH3:25])(=[O:41])=[O:42])[S:33][CH:34]=1)=[O:37]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2779163Methyl 5-(chlorosulfonyl)-4-methoxythiophene-3-carboxylateHCID 18430729HCID 18430729, compound

Product 1

HCID 54021354HCID 54021354, compoundYield 63.3%

Procedure

The title compound was prepared according to the procedure in Example 10, step 1, using 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-diethyl-phenol (0.604 g, 1.67 mmol), 60% sodium hydride/mineral oil (0.0669 g, 1.67 mmol) and 3-methoxy-4-(methoxycarbonyl)thiophene-2-sulphonylchloride (0.499 g, 1.84 mmol) to give 0.629 g (63%) of the title compound. 1H NMR (DMSO-d6) δ 1.10 (t, 6 H), 1.59 (s, 3 H), 2.42 (s, 3 H), 2.57-2.68 (m, 4 H), 3.86 (s, 3 H), 4.02 (s, 3 H), 7.20 (s, 2 H), 7.38-7.50 (m, 3 H), 7.98 (d, 1 H), 8.50 (s, 1 H), 8.81 (s, 1 H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-436c91783ce64acf8195f6fb9553a02d
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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