Isopropanol → Isopropyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

HRID 652027Notes

Reaction equation

HRID 652027 reaction equation
[CH3:1][Si:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.B(F)(F)F.CCOCC.[CH:38](O)([CH3:40])[CH3:39]>>[CH3:28][Si:2]([CH3:1])([CH3:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH:38]([CH3:40])[CH3:39])=[O:23])=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 8000Boron trifluoride etherateHCID 138848624-[14-(Trimethylsilyl)tetradecylamino)benzoic acid

Product 1

HCID 20198276Isopropyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Procedure

A solution of 4.9 g of 4-[14-(trimethylsilyl)tetradecylamino]benzoic acid and 3.4 ml. of boron trifluoride etherate in 20 ml. of isopropyl alcohol is stirred at reflux for 44 hours, allowed to cool, and poured into 120 ml. of ice cold 5% aqueous sodium carbonate solution. The white solid is collecetd by filtration and recrystallized from benzene-ethanol to yield the product as a white solid.

Workup

  1. temperatureat reflux for 44 hours
  2. temperatureto cool
  3. additionpoured into 120 ml
  4. filtrationThe white solid is collecetd by filtration
  5. customrecrystallized from benzene-ethanol

Sources & evidence

ORD record
ord-13d3015d12f34b3497202f0348528433
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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