HCID 22841014, compound → HCID 22841019, compound

HRID 329515Notes

Reaction equation

HRID 329515 reaction equation
C([O:8][CH2:9][C@H:10]1[C@@H:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:14][CH2:13][CH2:12][O:11]1)C1C=CC=CC=1>CO.C(O)C.[Pd]>[CH2:17]([O:16][C@H:15]1[CH2:14][CH2:13][CH2:12][O:11][C@H:10]1[CH2:9][OH:8])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 1

HCID 22841014HCID 22841014, compound

Product 1

HCID 22841019HCID 22841019, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

1.409 g of dl-cis-2-benzyloxymethyl-3-hexadecyloxytetrahydropyran (prepared as described in Preparation 45) was dissolved in 100 ml of a 1:1 by volume mixture of methanol and ethanol. 0.70 g of a 10% w/w palladium on activated carbon catalyst was then added to the resulting solution. Catalytic reduction using the same procedure as described in Preparation 44 yielded 1.116 g of a crude substance, which was then subjected to column chromatography through 30 g of silica gel. Those fractions eluted with mixtures of diethyl ether and hexane ranging from 1:20 to 1:5 by volume gave 1.031 g of the title compound, melting at 42°-43° C. (after recrystallisation from cold hexane).

Workup

  1. customas described in Preparation 44
  2. customyielded 1.116 g of a crude substance, which
  3. washThose fractions eluted with mixtures of diethyl ether and hexane ranging from 1:20 to 1:5 by volume
  4. customgave
  5. custom1.031 g of the title compound, melting at 42°-43° C. (after recrystallisation from cold hexane)

Sources & evidence

ORD record
ord-8aaa2d17a98b423f9cffdac9506d45f2
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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