Hydrochloric Acid → HCID 15405224, compound

HRID 443191Notes

Reaction equation

HRID 443191 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]1[CH:17]2[CH:12]([CH2:13][CH:14]([CH3:18])[CH2:15][CH2:16]2)[O:11][C:10](=[O:19])[CH2:9]1.Cl>CCOCC>[OH:19][CH2:10][CH2:9][CH:8]([CH3:7])[CH:17]1[CH2:16][CH2:15][CH:14]([CH3:18])[CH2:13][CH:12]1[OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13031558HCID 13031558, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15405224HCID 15405224, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Into a four-mouthflask (volume: 100 ml) in which the inside was replaced by nitrogen were supplied diethyl ether (hereinafter referred to as "ether") and lithium aluminum hydride (0.2 g, 5.5 mmol). To this solution was added dropwise at room temperature an ether solution of 5,9-dimethyl-2-oxabicyclo-[4,4,0]-decan-3-one (0.1 g, 0.55 mmol) which had been separately prepared. The mixture was allowed to react at the same temperature for 1 hour, and the reaction solution was poured into a 10% aqueous hydrochloric acid solution for separation. The ether layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The resultant crude product was purified by column chromatography on silica gel to give the title compound (2) (80 mg) (Theoretical yield: 78.1%). Analytical results on the title compound are given below.

Workup

  1. customhad been separately prepared
  2. customto react at the same temperature for 1 hour
  3. customThe ether layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe resultant crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-571fa44674d840d8835987358ffdb088
Source dataset
uspto-grants-1999_04
Patent number
US05892133

Reaction notes

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