Water → HCID 59139448, compound

HRID 2061136Notes

Reaction equation

HRID 2061136 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-1-3CO) (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-96b8842434f14cb2811bc5e849cd473e
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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