Dimethylformamide → HCID 15670655, compound

HRID 1650063Notes

Reaction equation

HRID 1650063 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[CH:13][C:14]=1[Br:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[C@@H:18]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)S([O-])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC.O>[Br:15][C:14]1[CH:13]=[CH:12][C:11]([O:16][C@H:23]([CH3:18])[CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 156706543-(Benzyloxy)-4-bromophenolHCID 86738785HCID 86738785, compound

Product 1

HCID 15670655HCID 15670655, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 21.8 g. (78 mmole) of 3-benzyloxy-4-bromophenol, 20.0 g. (82.6 mmole) of (S)-1-methyl-4-phenylbutylmethane sulfonate and 25.2 g. (200 mmole) of potassium carbonate in 100 ml. dimethylformamide was heated at 85° C. for 13.5 hours. The reaction was cooled and added to 500 ml. water-500 ml. ether. The organic extract was washed with two 250 ml. portions of water, dried over magnesium sulfate and evaporated to an oil. The crude oil was purified via column chromatography on 750 g. of silica gel eluted with 10% etherhexane to yield 23.9 g. (72%) of the title compound as an oil.

Workup

  1. additionA mixture of 21.8 g
  2. temperatureThe reaction was cooled
  3. additionadded to 500 ml
  4. extractionThe organic extract
  5. washwas washed with two 250 ml
  6. dry with materialportions of water, dried over magnesium sulfate
  7. customevaporated to an oil
  8. customThe crude oil was purified via column chromatography on 750 g
  9. washof silica gel eluted with 10% etherhexane
  10. customto yield 23.9 g

Sources & evidence

ORD record
ord-f0021150e84c4b8585c68f30248bcae8
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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