Hydrochloric Acid → HCID 86677103, compound

HRID 1427383Notes

Reaction equation

HRID 1427383 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C@H:7]([CH2:17][CH:18]=[CH2:19])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.Cl>O1CCCC1>[CH2:10]([O:9][CH2:8][C@H:7]([O:6][CH2:5][CH:4]=[O:3])[CH2:17][CH:18]=[CH2:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

Product 1

HCID 86677103HCID 86677103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

({[(2R)-2-(2,2-Diethoxyethoxy)pent-4-en-1-yl]oxy}methyl)benzene (C2) (10.14 g, 32.88 mmol) was dissolved in tetrahydrofuran (110 mL). Aqueous hydrochloric acid (2 M, 19.5 mL, 39.0 mmol) was added, and the reaction mixture was heated at 75° C. for 1 hour. The reaction was concentrated to approximately half the original volume and then partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was obtained as a colorless oil, which was used directly in the following step. Yield: 7.76 g. 1H NMR (400 MHz, CDCl3) δ 2.28-2.42 (m, 2H), 3.54-3.57 (m, 2H), 3.62-3.68 (m, 1H), 4.18-4.28 (m, 2H), 4.53 (br s, 2H), 5.06-5.15 (m, 2H), 5.78-5.89 (m, 1H), 7.27-7.39 (m, 5H), 9.72 (t, J=1.0 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated to approximately half the original volume
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was obtained as a colorless oil, which

Sources & evidence

ORD record
ord-d6b8c10bab4d4b11b75e8a3d147fb25f
Source dataset
uspto-grants-2015_01
Patent number
US08933221B2

Reaction notes

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