Dichloromethane → HCID 131734479, compound

HRID 590405Notes

Reaction equation

HRID 590405 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:29]=[CH:28][C:23]2[NH:24][C:25](=[O:27])[O:26][C:22]=2[CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][OH:39].C(Cl)Cl>CN(C=O)C.CCOCC>[Si:1]([O:18][CH2:19][C:20]1[CH:29]=[CH:28][C:23]2[N:24]([CH2:37][CH2:38][OH:39])[C:25](=[O:27])[O:26][C:22]=2[CH:21]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 131734478HCID 131734478, compound2×

Product 1

HCID 131734479HCID 131734479, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3-benzoxazol-2(3H)-one (Intermediate 78, 218 mg, 0.54 mmol) in DMF (2 mL) were added potassium carbonate (232 mg, 1.68 mmol) and 2-bromoethanol (60 μL, 0.85 mmol) and the reaction mixture was placed in a sealed vessel at 120° C. over a period of 4 hours. CH2Cl2 was added to the mixture and the solids were filtered off and washed with CH2Cl2. The resulting filtrate was washed with water and brine and the organic phase was filtered through a Phase Separator membrane to remove remaining water. The crude oil was purified by column chromatography over silica gel using Hexane:Et2O as eluent (from 0 to 100% of Et2O) to give the title compound as a white solid (107 mg, 44% yield).

Workup

  1. filtrationthe solids were filtered off
  2. washwashed with CH2Cl2
  3. washThe resulting filtrate was washed with water and brine
  4. filtrationthe organic phase was filtered through a Phase Separator membrane
  5. customto remove
  6. customThe crude oil was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-c0649d0f6feb4429a844a1096ae9fd55
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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