Hydrochloric Acid → HCID 18779098, compound

HRID 1422364Notes

Reaction equation

HRID 1422364 reaction equation
C([C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:8]([O:10]CCCl)=O)CCC.[Li+].[BH4-].Cl>C1COCC1.CCCCCC>[CH2:6]([C:6]1[CH:5]=[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:14][C:7]=1[CH2:8][OH:10])[CH2:5][CH2:16][CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 18779157HCID 18779157, compound

Product 1

HCID 18779098HCID 18779098, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a 100 mL round bottomed flask with a stirring bar and an argon inlet was added 2-chloroethyl 3-butyl-4-phenylbenzoate (570 mg, 1.80 mmol), THF (9 mL) and LiBH4 (9 mL of a 2M solution in THF, 18 mmol). This mixture was heated at reflux for 18 h. The cooled reaction mixture was treated with 1N HCl and extracted with EtOAc. The combined EtOAc extracts were washed with H2O and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. This material was chiromatographed on silica gel using 20% EtOAc in hexane as eluant to afford the title compound as a crystalline solid.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 18 h
  3. customThe cooled reaction mixture
  4. extractionextracted with EtOAc
  5. washThe combined EtOAc extracts were washed with H2O and brine
  6. customDrying
  7. filtration(MgSO4), filtration and removal of the solvent in vacuo
  8. customgave an oil

Sources & evidence

ORD record
ord-ada46f41271e4965ba47d428993b61d6
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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