Sodium Acetate → HCID 57149329, compound

HRID 1609179Notes

Reaction equation

HRID 1609179 reaction equation
BrC[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])=[CH:5][CH:4]=1.[C:24]([O-])(=[O:26])C.[Na+]>C(O)(=O)C>[OH:26][CH2:24][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)=[C:10]([C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:22])([CH3:23])[CH3:21])=[O:16])[CH:11]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 57229930HCID 57229930, compound

Product 1

HCID 57149329HCID 57149329, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.8 g of 4-bromomethyl-2'-(trimethylsilylethoxycarbonyl)biphenyl and 1.17 g of anhydrous sodium acetate are stirred overnight at 65° in glacial acetic acid and then boiled under reflux for 3 hours. The reaction mixture is evaporated, the residue is taken up in ethyl acetate and washed with water and sodium hydrogencarbonate, and the organic phase is dried and concentrated. The residue is introduced into 25 ml of ethanol, 6.3 ml of 1N NaOH are added and the mixture is stirred at room temperature for 30 minutes. It is evaporated in vacuo, and the residue is treated with ethyl acetate, washed with water and brine, dried and evaporated. Flash chromatography (N4) yields 4-hydroxymethyl-2-(trimethylsilylethoxycarbonyl)biphenyl as a colourless oil. 1H-NMR (DMSO): 0 ppm (s, 9H), 0.75 ppm (t, 2H), 4.1 ppm (t, 2H), 4.73 ppm (d, 2H), 5.27 ppm (t, 1H), 7.2-7.7 ppm aromatics.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe reaction mixture is evaporated
  3. washwashed with water and sodium hydrogencarbonate
  4. customthe organic phase is dried
  5. concentrationconcentrated
  6. additionThe residue is introduced into 25 ml of ethanol, 6.3 ml of 1N NaOH
  7. additionare added
  8. customIt is evaporated in vacuo
  9. additionthe residue is treated with ethyl acetate
  10. washwashed with water and brine
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-3d69eefd74ef4107b9afd81bc38e0cfd
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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