Ethyl Acetate → HCID 58070101, compound

HRID 1472298Notes

Reaction equation

HRID 1472298 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([OH:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].[Br:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26].C(OCC)(=O)C>C(Cl)Cl.O>[CH2:19]=[CH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([O:20][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][Br:21])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 702254-Bromobutyryl chlorideHCID 58069951HCID 58069951, compound

Product 1

HCID 58070101HCID 58070101, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol 11 (5.6 g, 20 mol) in anhydrous DCM (300 mL) was added slowly and carefully Bromobutryl chloride (20 mmol) at 0° C. under inert atmosphere. The reaction mixture was warmed to room temperature, stirred for 20 h and monitored by TLC (silica gel, 10% ethyl acetate in hexanes). Upon completion of the reaction, mixture was diluted with water (400 mL) and organic layer was separated out. Organic phase was then washed with sat. solution of NaHCO3 (1×400 mL) followed by brine (1×100 mL) and concentrated under vacuum. Crude product was then purified by silica gel (100-200 mesh) column, eluted with 2-3% ethyl acetate in hexane solution to give 6 g (90%) of desired product 12 as colorless liquid. 1H NMR (400 MHz, CDCl3) δ 5.80 (ddt, J=16.9, 10.2, 6.7 Hz, 2H), 5.05-4.81 (m, 5H), 3.46 (t, J=6.5 Hz, 2H), 2.48 (t, J=7.2 Hz, 2H), 2.17 (p, J=6.8 Hz, 2H), 2.11-1.93 (m, 4H), 1.65-1.44 (m, 4H), 1.43-1.17 (m, 19H). 13C NMR (101 MHz, cdcl3) δ 172.51, 139.37, 114.35, 77.54, 77.23, 76.91, 74.86, 34.31, 33.99, 33.01, 32.96, 29.65, 29.56, 29.24, 29.09, 28.11, 25.52.

Workup

  1. customat 0° C.
  2. customUpon completion of the reaction, mixture
  3. customwas separated out
  4. washOrganic phase was then washed with sat. solution of NaHCO3 (1×400 mL)
  5. concentrationconcentrated under vacuum
  6. customCrude product was then purified by silica gel (100-200 mesh) column
  7. washeluted with 2-3% ethyl acetate in hexane solution

Sources & evidence

ORD record
ord-ddbecc4d4c2247b2a5eb042d37d687c6
Source dataset
uspto-grants-2015_04
Patent number
US09012498B2

Reaction notes

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