Sodium Chloride → Ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

HRID 652017Notes

Reaction equation

HRID 652017 reaction equation
[CH3:1][Si:2]([CH3:31])([CH3:30])[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][C:16]([NH:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1)=O.B.[Cl-].[Na+]>O1CCCC1>[CH3:31][Si:2]([CH3:1])([CH3:30])[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:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6331BoraneHCID 13884859Ethyl 4-[14-(trimethylsilyl)tetradecanamido]benzoate

Product 1

HCID 13884860Ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 125 g. sample of ethyl 4-[14-(trimethylsilyl)tetradecanamido]benzoate was dissolved into 1 l. dry tetrahydrofuran, and to this stirred solution under nitrogen was dropwise added 419 ml. 1M borane in tetrahydrofuran. The solution was refluxed for four hours, cooled, and poured with stirring into 11.2 l. ice-water which contained about 250 g. sodium chloride. The precipitate was filtered off and air dried. Crystallization from ethanol afforded the pure product, m.p. 91°-92° C.

Workup

  1. temperatureThe solution was refluxed for four hours
  2. temperaturecooled
  3. additionpoured
  4. filtrationThe precipitate was filtered off
  5. customair dried
  6. customCrystallization from ethanol
  7. customafforded the pure product, m.p. 91°-92° C.

Sources & evidence

ORD record
ord-757fa412f72443db9a2d6d6f73c86689
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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