Sodium Hydroxide → HCID 68879751, compound

HRID 1454236Notes

Reaction equation

HRID 1454236 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([CH:16]=[O:17])[CH:13]=[CH:12][C:11]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[OH-].[Na+]>CO>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[CH:12][C:11]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86618491HCID 86618491, compound

Product 1

HCID 68879751HCID 68879751, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [2-(3,4-dichloro-phenoxy)-5-formyl-benzyl]-methyl-carbamic acid tert-butyl ester (816 mg, 1.98 mmol) in MeOH (40 mL), was added NaBH4 (75 mg, 1.98 mmol). After 24 h, the mixture was treated with 1 N NaOH, was stirred an additional 1 h, and then partially concentrated. The resulting aqueous mixture was extracted with DCM and the combined organic layers were dried (Na2SO4) and concentrated. The crude material was carried forward without further purification (784 mg, 96%). MS (ESI): mass calcd. for C20H23Cl2NO4, 411.10; m/z found, 434.7 [M+Na]+.

Workup

  1. concentrationpartially concentrated
  2. extractionThe resulting aqueous mixture was extracted with DCM
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude material was carried forward without further purification (784 mg, 96%)

Sources & evidence

ORD record
ord-ab3b07f3bc5a4362a69ba85742ef8077
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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