Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 10854265, compound

HRID 1071186Notes

Reaction equation

HRID 1071186 reaction equation
C1(C)C=CC=CC=1.[C:8]([O:12][C:13]([NH:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][CH:21](O)[CH2:20][CH2:19]2)=[O:14])([CH3:11])([CH3:10])[CH3:9].[C:27]([CH:32]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:29][CH2:30][CH3:31])=[O:28].[O-]CC.[Na+]>C1(C)C=CC=CC=1>[C:8]([O:12][C:13]([NH:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][CH:21]([CH2:32][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20][CH2:19]2)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester2×HCID 2723922Sodium ethoxide3×HCID 22471900HCID 22471900, compound

Product 1

HCID 10854265HCID 10854265, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into the 6-(tert-butyloxycarbonylamino)chroman-2-ol toluene solution of Example 2 (8 L) was added 1225 g of (carbethoxymethylene)triphenylphosphorane (95%) and 1.1 g of sodium ethoxide. The stirred reaction was heated to 80° C. for 2 h. An additional 3.2 g of sodium ethoxide was added, and the mixture stirred at 80° C. for 18 h. Because the reaction was not complete by TLC, an additional 122 g of (carbethoxymethylene)triphenylphosphorane and 1.0 g of sodium ethoxide was added. The reaction mixture was stirred at 80° C. for 3 h after the addition. The reaction was cooled to room temperature, and 3750 g of silica gel and 7 L of toluene were added. The mixture was stirred for 2 h, filtered, and the filter cake was washed with 2×12 L of toluene. The filtrate and washings were combined, and the volume reduced to about 7 L by distillation under reduced pressure (T≦60° C.) to provide a toluene solution of ethyl 2-(6-(tert-butyloxycarbonylamino)chroman-2-yl)acetate.

Workup

  1. customThe stirred reaction
  2. stirringThe reaction mixture was stirred at 80° C. for 3 h
  3. additionafter the addition
  4. temperatureThe reaction was cooled to room temperature
  5. stirringThe mixture was stirred for 2 h
  6. filtrationfiltered
  7. washthe filter cake was washed with 2×12 L of toluene
  8. distillationthe volume reduced to about 7 L by distillation under reduced pressure (T≦60° C.)

Sources & evidence

ORD record
ord-dadd56afb9074f2aa11cf828dace66d6
Source dataset
uspto-grants-2005_06
Patent number
US06903227B2

Reaction notes

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