Water → N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide

HRID 2089478Notes

Reaction equation

HRID 2089478 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([NH:12][C:13](=[O:15])[CH3:14])[CH:5]=[CH:4][C:3]1=2.[BH4-].[Na+].O>CO>[OH:1][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([NH:12][C:13](=[O:15])[CH3:14])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamideHCID 4311764Sodium borohydride

Product 1

HCID 67546890N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (1.00 g, 4.94 mmol) in methanol (20 mL) at 0° C. is added sodium borohydride (0.50 g, 7.41 mmol). The reaction is stirred for 1.5 hours, whereupon water is added and the volatiles are removed in vacuo. The mixture is extracted with dichloromethane and the organic phase is dried over sodium sulfate, filtered, and concentrated to give N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide, which is used in the next step without further purification.

Workup

  1. additionis added
  2. customthe volatiles are removed in vacuo
  3. extractionThe mixture is extracted with dichloromethane
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d860ab596fc4137991b6ac7a1e84a74
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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