Dicyclohexylcarbodiimide → (+)-4-[3-{2(S)-methylbutoxy}propyl]phenyl 4-decyloxybenzoate

HRID 257713Notes

Reaction equation

HRID 257713 reaction equation
[CH3:1][C@@H:2]([CH2:15][CH3:16])[CH2:3][O:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[CH2:17]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>>[CH2:17]([O:27][C:28]1[CH:29]=[CH:30][C:31]([C:32]([O:14][C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][CH2:5][O:4][CH2:3][C@@H:2]([CH3:1])[CH2:15][CH3:16])=[CH:13][CH:12]=2)=[O:33])=[CH:35][CH:36]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 1385274-(Decyloxy)benzoic acidHCID 22844682(+)-4-[3-{2(S)-methylbutoxy}propyl]phenol

Product 1

HCID 22844683(+)-4-[3-{2(S)-methylbutoxy}propyl]phenyl 4-decyloxybenzoateYield 90.4%

Procedure

Into a four-necked flask equipped with a stirrer and a thermometer were charged 1.11 g (5 millimole) of (+)-4-[3-{2(S)-methylbutoxy}propyl]phenol, 1.67 g (6 millimole) of 4-decyloxybenzoic acid and 30 ml of anhydrous dichlomethane, and then 1.22 g (6 millimole) of N,N'-dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine were added thereto, followed by stirring at room temperature for one day. After completion of the reaction, precipitates formed were filtered off and diluted with 200 ml of toluene. The organic phase was washed with water, 5% aqueous acetic acid solution, water, 5% aqueous sodium hydrogen carbonate solution and water in this order and then dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by silica gel column chromttography (eluent: toluene-ethyl acetate) to obtain 2.18 g (yield: 90.4%) of (+)-4-[3-{2(S)-methylbutoxy}propyl]phenyl 4-decyloxybenzoate.

Workup

  1. customInto a four-necked flask equipped with a stirrer
  2. customAfter completion of the reaction
  3. customprecipitates
  4. customformed
  5. filtrationwere filtered off
  6. additiondiluted with 200 ml of toluene
  7. washThe organic phase was washed with water, 5% aqueous acetic acid solution, water, 5% aqueous sodium hydrogen carbonate solution and water in this order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromttography (eluent: toluene-ethyl acetate)

Sources & evidence

ORD record
ord-808005c4d12d4f4fa01d6268e9eeae2f
Source dataset
uspto-grants-1993_11
Patent number
US05264151

Reaction notes

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