Acetic Acid → HCID 57014251, compound

HRID 728208Notes

Reaction equation

HRID 728208 reaction equation
C([O:8][C@H:9]1[CH2:15][C@@H:14]([O:16][CH3:17])[C:13]2([CH2:19][CH3:20])[O:18][C@@H:10]1[CH2:11][O:12]2)C1C=CC=CC=1.C(O)(=O)C.[H][H]>C(O)C.[Pd]>[CH2:19]([C:13]12[O:18][C@H:10]([CH2:11][O:12]1)[C@@H:9]([OH:8])[CH2:15][C@H:14]2[O:16][CH3:17])[CH3:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 57043201HCID 57043201, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57014251HCID 57014251, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (1R,2S,4R)-2-benzyloxy-5-ethyl-4-methoxy-6,8-dioxabicyclo[3.2.1]octane (see Example 15.2) (3.4 g) in absolute ethanol (150 ml) containing acetic acid (2 ml) and 5% palladium on barium sulphate (1 g) was shaken in a hydrogen atmosphere at 40 p.s.i for 24 h, and then the solution was filtered and the solvent was removed. Chromatography of the residue on silica gel gave the title alcohol; m.p. 52°-53° C.; [α]D -97.1°; 13C nmr data: 108.2 (C-5), 78.7 and 78.0 (C-1 and C-4), 66.9 (C-2), 66.3 (C-7), 57.6 (OCH3), 27.0 and 26.0 (C-3 and CH2CH3), and 6.4 (CH2CH3).

Workup

  1. filtrationthe solution was filtered
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-2d1997af0ec74a0b97cb882bb8d29036
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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