Water → HCID 15213644, compound

HRID 458070Notes

Reaction equation

HRID 458070 reaction equation
[H-].[Na+].C([O:7][C:8](=[O:18])[CH2:9][CH:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11](O)=O)(C)(C)C.O>C1COCC1>[CH2:14]([CH:10]1[CH2:11][O:18][C:8](=[O:7])[CH2:9]1)[CH:15]([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 99427122-Isobutyl-succinic acid-4-t-butyl ester

Product 1

HCID 15213644HCID 15213644, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethyl phosphonoacetate (1.13 mL, 5.70 mmol) was added dropwise to a stirring suspension of sodium hydride (0.22 g of a 60% dispersion in oil, 5.43 mmol) in THF (15 mL) at 0° C. under argon. After 20 minutes, ketone 3 (0.75 g, 5.43 mmol) in THF (6 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 16 hours. Water (5 mL) was added, and the mixture was extracted with ether (15 mL×3). The combined organic fractions were washed with brine and dried (MgSO4). The solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5) to give the ester 4 (0.81 g, 72%) as a colorless oil; Rf(heptane/ethyl acetate, 8:2) 0.66; νmax(film)/cm−1 1715 (C═O), 1652 (C═C); δH (400 MHz; CDCl3): 5.80 (1H, quint, J=2.2, CHCO2Et), 4.15 (2H, q, J=7.1, CO2CH2Me), 2.79 (1H, dd, J=19.5, 8.1), 2.69 (1H, ddt, J=19.8, 7.3, 2.3), 2.47 (1H, dd, J=17.3, 7.2), 2.34 (1H, ddt, J=17.3, 5.6, 1.8), 2.14 (1H, m), 2.02 (1H, m), 1.60–1.22 (8H, m); m/z (ES+) 209 (M+H, 57%), 455 (2M+K, 67).

Workup

  1. extractionthe mixture was extracted with ether (15 mL×3)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-90e800f79c6749d780c5b56ab4394afa
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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