HCID 22841014, compound → HCID 22841019, compound

HRID 414779Notes

Reaction equation

HRID 414779 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 10) 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 8 yielded 1.116 g of a crude substance, which was then subjected to column chromatography through 30 g of silica gel. The fraction 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. (cold hexane).

Workup

  1. customas described in Preparation 8
  2. customyielded 1.116 g of a crude substance, which
  3. washThe fraction eluted with mixtures of diethyl ether and hexane ranging from 1:20 to 1:5 by volume

Sources & evidence

ORD record
ord-6b9f1c783bb24cd4a67843f496ebe5d0
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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