Water → HCID 5494880, compound

HRID 841100Notes

Reaction equation

HRID 841100 reaction equation
[CH3:1][C:2]1([CH3:25])[O:7][C:6]2[C:8]3[C:13]([CH2:14][CH2:15][CH3:16])=[CH:12][C:11](=[O:17])[O:10][C:9]=3[CH:18]=[C:19]([O:20]C(=O)CC)[C:5]=2[CH:4]=[CH:3]1.C([O-])(O)=O.[Na+].O>CO>[CH3:25][C:2]1([CH3:1])[O:7][C:6]2[C:8]3[C:13]([CH2:14][CH2:15][CH3:16])=[CH:12][C:11](=[O:17])[O:10][C:9]=3[CH:18]=[C:19]([OH:20])[C:5]=2[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 502055HCID 502055, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 5494880HCID 5494880, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ester 5a (223 mg, 0.65 mmol) in 15 mL of MeOH were added saturated aqueous solution of NaHCO3 (7 mL) and water (7 mL). The reaction mixture was stirred at room temperature under nitrogen for 7 h until TLC indicated complete consumption of the starting material. The reaction mixture was then acidified with 10% aqueous HCl (100 mL), and extracted with EtOAc (50 mL). The organic solution was washed with brine (100 mL) and dried with Na2SO4. Evaporation of the solvent yielded the crude product that was purified by preparative TLC to afford 97 mg (52% yield) of 6 as a solid. mp 190-192° C.; 1H NMR (DMSO-d6) δ 0.99 (3H, t, J=7.3 Hz), 1.45 (6H, s), 1.59 (2H, m), 2.83 (2H, t, J=7.6 Hz), 5.66 (1H, d, J=9.9 Hz), 5.92 (1H, s), 6.34 (1H, s), 6.57 (1H, d, J=9.9 Hz), 10.77 (1H, s); 13C NMR (DMSO-d6) δ 13.7, 22.9, 27.2, 37.5, 77.5, 95.7, 102.2, 106.1, 109.9, 116.3, 127.1, 151.7, 155.7, 156.4, 157.8, 160.0, 188.9; IR (film): 3185, 1686, 1582, 1381, 1157 cm−1; MS m/e: 287 (M+1); Anal. Calcd. for C17H18O4: C, 71.31; H, 6.34. Found: C, 71.39; H, 6.40.

Workup

  1. customconsumption of the starting material
  2. extractionextracted with EtOAc (50 mL)
  3. washThe organic solution was washed with brine (100 mL)
  4. dry with materialdried with Na2SO4
  5. customEvaporation of the solvent
  6. customyielded the crude product that
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-10ab77129577472fb0763abe6de9c2e9
Source dataset
uspto-grants-2002_04
Patent number
US06369241B1

Reaction notes

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