Hydrochloric Acid → 2,2-Dimethyl-3-(tetrahydro-furan-3-yloxy)-propan-1-ol

HRID 1046444Notes

Reaction equation

HRID 1046444 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12](=O)[C:13]([CH3:22])([CH3:21])[CH2:14][O:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1.Cl>ClCCl>[CH3:21][C:13]([CH3:22])([CH2:14][O:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1)[CH2:12][OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydride2×HCID 58114071Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester

Product 1

HCID 668501482,2-Dimethyl-3-(tetrahydro-furan-3-yloxy)-propan-1-olYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

DIBAL (1.74 mL of a 1.0 M solution in hexanes) was added dropwise to a solution of 2,2-dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester (353 mg, 1.74 mmol) in dichloromethane (9.0 mL) at −78° C. After 2 h at this temperature, an additional equivalent of DIBAL was added and after 1 h the reaction was warmed to 0° C. After an additional 1 h at 0° C., 1.0 N HCl was added dropwise to quench the reaction. The reaction was warmed to room temperature and partitioned between dichloromethane and brine. The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated to give an oil. Purification by flash column chromatography on silica gel using 50% ethyl acetate in hexanes provided 2,2-dimethyl-3-(tetrahydro-furan-3-yloxy)-propan-1-ol (250 mg, 82%) as a colorless oil.

Workup

  1. waitAfter an additional 1 h at 0° C.
  2. customto quench
  3. customthe reaction
  4. temperatureThe reaction was warmed to room temperature
  5. custompartitioned between dichloromethane and brine
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with dichloromethane
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. concentrationconcentrated
  10. customto give an oil
  11. customPurification by flash column chromatography on silica gel using 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-495bdd5baf224f5aaa9e09bc3566cdd4
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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