Sodium Hydroxide → HCID 23360888, compound

HRID 232782Notes

Reaction equation

HRID 232782 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([OH:19])[CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[OH:19][C:8]1[CH:9]=[C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([OH:2])[CH:12]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromide2×HCID 10400344HCID 10400344, compound

Product 1

HCID 23360888HCID 23360888, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 0.2 g (0.771 mmol) of N-[2-(7-methoxy-3-hydroxynaphth-1-yl)ethyl]acetamide, according to Example 77, in 5 cm3 of anhydrous dichloromethane. Cool in a bath of ice and salt. Add dropwise 0.8 cm3 of 1M boron tribromide. Stir in ice at room temperature for 4 hours. Add a further 0.8 cm3 of 1M boron tribromide in CH2CL2. Allow to stir overnight at room temperature. Bring to pH 8 with 1N NaOH. Extract with CH2Cl2. Dry with MgSO4. Evaporate off the solvent. Recover the product. Extract with methyl ethyl ketone. Dry over MgSO4. Evaporate off the solvent. Purify the product on 30 g of silica. Elute with CH2Cl2 /MeOH: 95/5. The product of Example 78 is obtained.

Workup

  1. temperatureCool in a bath of ice and salt
  2. stirringAllow to stir overnight at room temperature
  3. extractionExtract with CH2Cl2
  4. dry with materialDry with MgSO4
  5. customEvaporate off the solvent
  6. customRecover the product
  7. extractionExtract with methyl ethyl ketone
  8. dry with materialDry over MgSO4
  9. customEvaporate off the solvent
  10. customPurify the product on 30 g of silica
  11. washElute with CH2Cl2 /MeOH

Sources & evidence

ORD record
ord-4428fe0923ba45e88e65aa9886ddc468
Source dataset
uspto-grants-1997_01
Patent number
US05591775

Reaction notes

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