Ethanol → HCID 10597413, compound

HRID 431294Notes

Reaction equation

HRID 431294 reaction equation
[BH4-].[Na+].CCO.[CH3:6][CH:7]([O:21][C:22]([O:24][C:25]1[C:32]([CH3:33])=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][C:26]=1[CH3:34])=[O:23])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19]>C(Cl)Cl>[CH3:6][CH:7]([O:21][C:22]([O:24][C:25]1[C:26]([CH3:34])=[CH:27][C:28]([CH2:29][OH:30])=[CH:31][C:32]=1[CH3:33])=[O:23])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 11795431HCID 11795431, compound

Product 1

HCID 10597413HCID 10597413, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (9 ing, 0.25 inmol) followed by EtOH (0.5 mL) was added to 7k (100 mg, 0.25 mmol) in CH2Cl2 (2 mL) at r.t. and then refluxed for 30 minutes. Aqueous workup (CH2Cl2, MgSO4) followed by concentration in vacuo yielded 8k (75 mg, 75%) as a light yellow solid: 1H NMR (270 MHz, CDCl3) d 1.68 (d, J=6.4 Hz, 3H), 2.03 (s, 6H), 3.86 (s, 3H), 3.91 (s, 3H), 4.45 (s, 2H), 6.39 (q, J=6.4 Hz, 1H), 6.92 (s, 2H), 7.06 (s, 1H), 7.52 (s, 1H); 13C NMR (68 MHz, CDCl3) d 16.0, 21.9, 56.3, 56.4, 64.4, 73.0, 107.4, 107.6, 127.2, 129.9, 132.3, 138.7, 139.8, 147.4, 148.1, 151.7, 153.7.

Workup

  1. temperaturerefluxed for 30 minutes
  2. concentrationAqueous workup (CH2Cl2, MgSO4) followed by concentration in vacuo

Sources & evidence

ORD record
ord-bd419d71530440ec9ff4aa6d1a68d5f6
Source dataset
uspto-grants-2003_12
Patent number
US06657052B1

Reaction notes

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