Crotyl chloride → HCID 69268623, compound

HRID 2224830Notes

Reaction equation

HRID 2224830 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](Cl)[CH:20]=[CH:21][CH3:22].[I-].[Li+].C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>O1CCCC1>[CH3:11][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH2:19]/[CH:20]=[CH:21]/[CH3:22])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:18]

Participants

6

Reactant 4

HCID 11589Crotyl chlorideHCID 66321Lithium iodideHCID 2733832Lithium HexamethyldisilazideHCID 14494047HCID 14494047, compound

Product 1

HCID 69268623HCID 69268623, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-phenyl-propionic acid benzyl ester (2.0 g, 8.32 mmol), crotyl chloride (1.02 mL, 9.99 mmol), and lithium iodide (1 g) in tetrahydrofuran (15 mL) at 0° C. was treated dropwise with the lithium hexamethyldisilazide (9.99 mL, 1M in tetrahydrofuran, 9.99 mmol). The reaction was allowed to warm to 25° C. and stirred for 18 hours. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the ethyl acetate layers were combined, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane, then 10% ethyl acetate in hexane, and 20% ethyl acetate in hexane to give the title compound (2.43 g, 99%). 1H NMR (300 MHz, CDCl3): δ ppm 1.55 (m, 6 H) 2.68 (m, 2 H) 5.10 (m, 2 H) 5.21 (m, 1 H) 5.45 (m, 1 H) 7.26 (m, 10 H). MS (ESI+) m/z 312 (M+NH4)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with hexane

Sources & evidence

ORD record
ord-d8b77ec0f6da48b5b00427afda1705d2
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

Loading…