Water → HCID 59139448, compound

HRID 1046807Notes

Reaction equation

HRID 1046807 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([O:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:6][C:7]2[O:12][C:11](=[O:13])[C:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)=[C:9]([CH2:24][C:25](=[O:27])[CH3:26])[C:8]=2[CH:28]=1.O>C1COCC1>[Cl:3][C:4]1[C:5]([O:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:6][C:7]2[O:12][C:11](=[O:13])[C:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)=[C:9]([CH2:24][CH:25]([OH:27])[CH3:26])[C:8]=2[CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59139370HCID 59139370, compound

Product 1

HCID 59139448HCID 59139448, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (49 mg, 1.30 mmol) was added to a solution of dimethylcarbamic acid 6-chloro-3-(3-nitrobenzyl)-2-oxo-4-(2-oxopropyl)-2H-1-benzopyran-7-yl ester (compound 7f-1-3 CO) (300 mg, 0.65 mmol) in anhydrous THF (5.0 mL), and the mixture was stirred at 0° C. for 2 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate, and the title compound (280 mg, 93%) was obtained as a pale yellow powder.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated saline
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-a4976ae0a6584f3e96cb01ab3f6262dc
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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