Dimethylformamide → HCID 15670655, compound

HRID 1758166Notes

Reaction equation

HRID 1758166 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.CS(O[C@@H:22]([CH3:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)=O.C(=O)([O-])[O-].CN(C)C=O>CCOCC.O>[Br:15][C:14]1[CH:13]=[CH:12][C:11]([O:16][C@H:22]([CH3:32])[CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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 19660Carbonate IonHCID 12878387HCID 12878387, compoundHCID 156706543-(Benzyloxy)-4-bromophenol

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-phenylbutyl methane sulfonate and 25.2 g. (200 mmole) of potassijm 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% ether-hexane 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% ether-hexane
  10. customto yield 23.9 g

Sources & evidence

ORD record
ord-561a9a20f7264afeae31936999411acd
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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