Ammonium Chloride → (2R)-1-(benzyloxy)pent-4-en-2-ol

HRID 1427381Notes

Reaction equation

HRID 1427381 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:13]([Mg]Cl)=[CH2:14].[Cl-].[NH4+]>C(OCC)C.[Cu]I>[CH2:1]([O:8][CH2:9][C@H:10]([OH:11])[CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 159746(-)-Benzyl (R)-glycidyl etherHCID 178461836HCID 178461836, compound

Product 1

HCID 10375318(2R)-1-(benzyloxy)pent-4-en-2-ol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of (2R)-2-[(benzyloxy)methyl]oxirane (9.8 g, 60 mmol) and copper(I) iodide (648 mg, 3.40 mmol) in diethyl ether (150 mL) was cooled to −78° C. Vinylmagnesium chloride (1.6 M solution in tetrahydrofuran; 41.0 mL, 65.6 mmol) was added drop-wise, and the reaction mixture was allowed to warm slowly to room temperature and stir for 18 hours. Ice and saturated aqueous ammonium chloride solution were added, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with aqueous ammonium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. This material was used in the following step without further purification. 1H NMR (400 MHz, CDCl3), product peaks only: δ 2.25-2.31 (m, 2H), 3.39 (dd, J=9.4, 7.4 Hz, 1H), 3.53 (dd, J=9.5, 3.4 Hz, 1H), 3.87-3.93 (m, 1H), 4.57 (s, 2H), 5.09-5.16 (m, 2H), 5.78-5.89 (m, 1H), 7.3-7.4 (m, 5H).

Workup

  1. temperatureto warm slowly to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with aqueous ammonium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThis material was used in the following step without further purification

Sources & evidence

ORD record
ord-b9247bdc157a423b956c951f43749a00
Source dataset
uspto-grants-2015_01
Patent number
US08933221B2

Reaction notes

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