Hydrochloric Acid → HCID 67862685, compound

HRID 258448Notes

Reaction equation

HRID 258448 reaction equation
[CH2:1]([O:8][C@@H:9]([C:16]#[C:17][C@@H:18]([OH:33])[C@@H:19]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>O1CCCC1.O.C(O)C>[CH2:1]([O:8][C@@H:9]([CH:16]=[CH:17][C@@H:18]([OH:33])[C@@H:19]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10906545HCID 10906545, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 67862685HCID 67862685, compoundYield 81.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 654 mg (1.44 mM) of (3R,6R, 7S) 3,7-dibenzyloxy-1,1-dimethoxydodeca-4-yn-6-ol [3b] described above in 10 ml of anhydrous tetrahydrofuran was dropwise added at 0° C. to a suspension of 115.7 mg (3.02 mM) of lithium aluminum hydride in 5 ml of anhydrous tetrahydrofuran, the mixture was stirred for 18 minutes under reflux. After completion of the reaction, ethyl acetate, ethanol, water and 0.1 N hydrochloric acid were added in sequence. Then, the aqueous phase was extracted with diethyl ether 3 times. The extracts were combined and washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and 538 mg (1.18 mM) of (3R,6R,7S) 3,7-dibenzyloxy-1,1-dimethoxydodeca-4-en-6-ol [5] was obtained from the fraction eluted with diethyl ether:hexane=1:3. Yield, 82%.

Workup

  1. temperatureunder reflux
  2. additionwere added in sequence
  3. extractionThen, the aqueous phase was extracted with diethyl ether 3 times
  4. washwashed with saturated sodium chloride aqueous solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3c84c7d6a6ee4f8dab1bb82658f432bf
Source dataset
uspto-grants-1993_11
Patent number
US05266703

Reaction notes

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