Benzyl Alcohol → HCID 58282620, compound

HRID 925924Notes

Reaction equation

HRID 925924 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:11][CH2:10][C@@H:9]2[CH2:12][C@H:6]1[C:7](=[O:13])[O:8]2)=[O:4].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=[O:23].[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:11][CH2:10][C@@H:9]([OH:8])[CH2:12][C@H:6]1[C:7]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:23])=[O:4]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 56605006HCID 56605006, compound

Product 1

HCID 58282620HCID 58282620, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound 34c (1.85 g, 1 eq.), in dry DMF (10 mL) were added benzyl alcohol (1.25 mL, 1.2 eq.) and K2CO3 (2.8 g, 2 eq.). The reaction mixture was stirred for 16 hrs under nitrogen. Water was then added and the reaction was extracted with TBDME. The combined organic layers were washed with brine, dried over MgSO4, concentrated under reduced pressure, and purified by chromatography on silica gel (DCM/MeOH) to yield compound 34d as beige solid in 70% yield.

Workup

  1. extractionthe reaction was extracted with TBDME
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by chromatography on silica gel (DCM/MeOH)

Sources & evidence

ORD record
ord-4ad20a8a3d264a28a38ad6c64e1a4bdb
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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