Hydrochloric Acid → HCID 53922310, compound

HRID 1755815Notes

Reaction equation

HRID 1755815 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:19][CH:18]=[C:17]([O:20]C)[CH2:16][CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86748874HCID 86748874, compound

Product 1

HCID 53922310HCID 53922310, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a vigorously stirred solution of the above diene (32) (44.2 g) in ethyl acetate (250 mL) was added aqueous 1N HCl (250 mL). After stirring for 1 h the ethyl acetate phase was removed, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (33) was obtained by flash chromatography on silica gel eluted with 35% ethyl acetate in n-hexane (39.69 g, 91%). TLC Rf 0.51 (30% ethyl acetate, n-hexane); 1H NMR (CDCl3)δ1.25(3H, d, J=7 Hz), 2.44(4H, br s), 2.88(2H, br s), 4.35(1H, q), 4.95(1H, br d), 5.13(2H, s), 5.72(1H, t), 7.38(5H, s).

Workup

  1. customwas removed
  2. washwashed with saturated NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-07e8ed2c36ac45abbc17d0fba3529db8
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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