Hydrochloric Acid → HCID 19746847, compound

HRID 2253928Notes

Reaction equation

HRID 2253928 reaction equation
[CH2:1]([C:4]([OH:25])([CH2:22][CH:23]=[CH2:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])[CH:2]=[CH2:3].Cl.[CH3:27]COCC>>[CH2:1]([C:4]([OH:25])([CH2:22][CH:23]=[CH2:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([CH3:20])([CH3:21])[C:17]([O:19][CH3:27])=[O:18])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 19746852HCID 19746852, compound

Product 1

HCID 19746847HCID 19746847, compound

Procedure

A cooled ether solution of 2.4 g of the product of Example 8 was added to excess CH2N2 in ether at 0° to 5°; after standing 2 hours, the excess CH2N2 was decomposed with dilute HCl. The ether layer was washed with H2O, with dilute NaHCO3, dried (K2CO3) and evaporated. The residue, 2.5 g, was flash chromatographed on a 10×20 cm column of silica gel in 20% C2H5OCOCH3 --CH2Cl2 ; a single fraction of 0.37 g was used for; a total of 1.35 g of title compound was obtained as a light yellow oil.

Workup

  1. washThe ether layer was washed with H2O, with dilute NaHCO3
  2. dry with materialdried (K2CO3)
  3. customevaporated
  4. customchromatographed on a 10×20 cm column of silica gel in 20% C2H5OCOCH3

Sources & evidence

ORD record
ord-9a1c46bad3cf4d64ba3bb55d6ac03300
Source dataset
uspto-grants-1993_08
Patent number
US05233063

Reaction notes

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