Diethyl Ether → HCID 19606158, compound

HRID 1603824Notes

Reaction equation

HRID 1603824 reaction equation
O[CH:2]([CH2:5][CH:6]=[CH2:7])[CH2:3][CH3:4].[CH3:8][CH2:9][O:10][C:11](/[C:13](/Cl)=[N:14]\[OH:15])=[O:12].C(N(CC)CC)C.C([O:26]CC)C>>[C:11]([C:13]1[CH2:4][CH:3]([CH2:2][CH2:5][CH:6]([OH:26])[CH3:7])[O:15][N:14]=1)([O:10][CH2:9][CH3:8])=[O:12]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 136489Hex-5-en-3-olHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 19606158HCID 19606158, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 6 g of 3-hydroxy-5-hexene in 150 ml of diethyl ether was added 18.1 g of ethyl chlorooximidoacetate. The solution was cooled to 0° C., and a solution of 21 ml of triethylamine in 210 ml of diethyl ether was added over 2.5 h. The amine hydrochloride salt was filtered and the residue was purified by silica gel column chromatography (5% to 10% EtOAc in CH2Cl2) to provide 5.5 g of desired product. 1H NMR (CDCl3): δ 0.96 (t, 3 H), 1.47 (t, 3 H), 1.50-1.95 (m, 4 H), 2.90 (m, 1 H), 3.35 (m, 1 H), 3.80 (m, 1 H), 4.35 (q, 2 H), 5.02 (m, 1 H).

Workup

  1. filtrationThe amine hydrochloride salt was filtered
  2. customthe residue was purified by silica gel column chromatography (5% to 10% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-474b7b22d1904326a1e202d9de180657
Source dataset
uspto-grants-1999_11
Patent number
US05990135

Reaction notes

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