Hydrochloric Acid → HCID 59464267, compound

HRID 1713864Notes

Reaction equation

HRID 1713864 reaction equation
Cl.O1[C:6]2([CH2:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[O:5]CC1>C1COCC1>[O:5]=[C:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59464079HCID 59464079, compound

Product 1

HCID 59464267HCID 59464267, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous HCl (1.15 mL of a 2M solution) was added to a stirred solution of diethyl [4-(1,4-dioxaspiro[4.5]dec-8-yl)phenyl]malonate (290 mg, 0.77 mmol) in 4 mL THF. The mixture was stirred for 64 h then was partitioned between water and EtOAc. The organic phase was separated and the aqueous further extracted with EtOAc. The organics were combined and dried then concentrated by evaporation to give the title compound (249 mg, 97%) as a gum; 1H NMR δ 1.18 (6H, t), 1.82-1.93 (2H, m), 2.06-2.11 (2H, m), 2.26-2.29 (2H, m), 2.54-2.63 (2H, m), 3.04-3.10 (1H, m), 4.08-4.21 (4H, m), 4.88 (1H, s), 7.31 (4H, s); MS m/e M+Na+ 355.

Workup

  1. customthen was partitioned between water and EtOAc
  2. customThe organic phase was separated
  3. extractionthe aqueous further extracted with EtOAc
  4. customdried
  5. concentrationthen concentrated by evaporation

Sources & evidence

ORD record
ord-4d442996cfb64e7586450e0fb89b3c3e
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…