Ethyl Acetate → HCID 86610088, compound

HRID 1435568Notes

Reaction equation

HRID 1435568 reaction equation
C([O:5][C:6](=[O:9])[CH2:7]Br)(C)(C)C.[CH2:10]([O:17][CH2:18][CH:19]([CH2:45][O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[O:20][CH2:21][CH:22](O)[CH2:23][O:24][CH:25]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+].C(OCC)(=O)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[CH2:47]([O:46][CH2:45][CH:19]([CH2:18][O:17][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[O:20][CH2:21][CH:22]([CH2:7][C:6]([OH:9])=[O:5])[CH2:23][O:24][CH:25]([CH2:26][O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 79177tert-Butyl bromoacetateHCID 15722252HCID 15722252, compound

Product 1

HCID 86610088HCID 86610088, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

14.62 g (75 mmol) of bromoacetic acid-tert-butyl ester is added [to] 30.02 g (50 mmol) of 1,3-bis-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-propan-2-ol (Cassel et al., Eur. J. Org. Chem., 2001, 5, 875-896) and 5.6 g (100 mmol) of fine-powder potassium hydroxide as well as a catalytic amount (1 g) of tetra-n-butylammonium hydrogen sulfate in 250 ml of toluene at 0° C., and it is stirred for 2 hours at this temperature as well as for 12 hours at room temperature. The reaction solution is mixed with 500 ml of ethyl acetate and 300 ml of water. The organic phase is separated and washed twice with 300 ml each of water, then dried on magnesium sulfate and evaporated to the dry state in a vacuum. The residue is suspended in a mixture consisting of 400 ml of methanol and 0.5 M sodium hydroxide solution at a 2:1 ratio and then heated for 12 hours to 60° C. The reaction mixture is neutralized for working-up by mixing with Amberlite IR 120 (H+ form)-cation exchange resin, exchanger is filtered out, evaporated to the dry state, and chromatographed on silica gel (mobile solvent: ethyl acetate/hexane 1:3).

Workup

  1. customThe organic phase is separated
  2. washwashed twice with 300 ml each of water
  3. customdried on magnesium sulfate
  4. customevaporated to the dry state in a vacuum
  5. temperatureheated for 12 hours to 60° C
  6. additionby mixing with Amberlite IR 120 (H+ form)-cation exchange resin, exchanger
  7. filtrationis filtered out
  8. customevaporated to the dry state
  9. customchromatographed on silica gel (mobile solvent: ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-5b4cf0f7d6d34b269c27a095fd068a63
Source dataset
uspto-grants-2009_11
Patent number
US07618957B2

Reaction notes

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