Water → HCID 76571136, compound

HRID 2108935Notes

Reaction equation

HRID 2108935 reaction equation
[CH3:1][C:2]1([CH2:21][CH2:22][CH:23]=[C:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:20])[C:6]([CH3:19])=[C:7]([O:12]C3CCCCO3)[CH:8]=2)[O:3]1.O>CO.Cl>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[C:5]([CH3:20])[C:6]=1[CH3:19])[O:3][C:2]([CH2:21][CH2:22][CH:23]=[C:24]1[S:28][C:27](=[O:29])[NH:26][C:25]1=[O:30])([CH3:1])[CH2:11][CH2:10]2

Participants

5

Reactant 2

HCID 962WaterHCID 86597205HCID 86597205, compound

Product 1

HCID 76571136HCID 76571136, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-{(3-[2,7,8-trimethyl-6-(tetrahydro-pyran-2-yloxy)-chroman-2-yl]-propylidene}-thiazolidine-2,4-dione from Step 3 (155 mg) in MeOH (10 mL) were added 10 drops of conc. HCl, and the mixture was stirred at RT for 3 h, then poured into water and extracted with EtOAc. The crude product was purified by silica gel column chromatography eluting with 30-40% EtOAc in hexane to give 5-[3-(6-hydroxy-2,7,8-trimethyl-chroman-2-yl)-propylidene]-thiazolidine-2,4-dione. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.08 (t, J=7.6 MHz, 1H), 6.38 (s, 1H), 2.70 (m, 2H), 2.37 (m, 2H), 2.14, 2.11 (2 s, 6H), 2.00-0.180 (m, 4H), 1.25 (s, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ (ppm): 171.45, 167.17, 165.43, 146.63, 145.06, 139.75, 126.04, 125.86, 122.03, 117.81, 112.20, 74.41, 60.53, 37.52, 31.51, 26.30, 23.74, 22.06, 21.09, 14.18, 12.00, 11.90 ppm. MS (m/z):348 (M+H+), 370 (M+Na+).

Workup

  1. extractionextracted with EtOAc
  2. customThe crude product was purified by silica gel column chromatography
  3. washeluting with 30-40% EtOAc in hexane

Sources & evidence

ORD record
ord-05ee1eaecc224d2599250c71f75d07ed
Source dataset
uspto-grants-2009_04
Patent number
US07514461B2

Reaction notes

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