(1S)-1-(2-chlorophenyl)ethan-1-ol → Methyl 3-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-nitro-2-thiophenecarboxylate

HRID 736358Notes

Reaction equation

HRID 736358 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[S:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C@@H:21](O)[CH3:22]>>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C@H:21]([O:1][C:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[S:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11])[CH3:22]

Participants

3

Reactant 2

HCID 6999091(1S)-1-(2-chlorophenyl)ethan-1-olHCID 54691283Methyl 3-hydroxy-5-nitrothiophene-2-carboxylate

Product 1

HCID 57848957Methyl 3-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-nitro-2-thiophenecarboxylate

Procedure

Methyl 3-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-nitro-2-thiophenecarboxylate was prepared from methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate and (1S)-1-(2-chlorophenyl)ethanol by a procedure analogous to Intermediate Example 1, Step A. 1H NMR (400 MHz, DMSO-d6): δ 7.96 (s, 1H), 7.65 (dd, 1H, J=1.7, 7.8 Hz), 7.47 (dd, 1H, J=1.5, 7.7 Hz), 7.40 (dt, 1H, J=1.3, 7.5 Hz), 7.34 (dt, 1H, J=1.9, 7.5 Hz), 5.98 (q, 1H, J=6.0 Hz), 3.85 (s, 3H), 1.59 (d, 3H, J=6.2 Hz).

Sources & evidence

ORD record
ord-99ab93234a8b449aaf2d0f87bc5504e0
Source dataset
uspto-grants-2009_09
Patent number
US07595330B2

Reaction notes

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