Hydrochloric Acid → HCID 69518655, compound

HRID 855099Notes

Reaction equation

HRID 855099 reaction equation
C[O:2][C:3]1[CH:4]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2.OO.[OH-].[Na+].Cl.[CH2:36]1COCC1>O>[OH:2][C:3]1[CH:12]=[C:7]2[C:6](=[C:5]([CH3:36])[CH:4]=1)[O:11][CH:10]([C:13]([F:15])([F:14])[F:16])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69517828HCID 69517828, compound

Product 1

HCID 69518655HCID 69518655, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The ethyl 8-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate (1.62 g, 3.92 mmole) was dissolved in THF (25 mL) and cooled to 0° C. (ice bath). Hydrogen peroxide (0.67 g, 5.88 mmole) followed by 2.5 N sodium hydroxide (1.57 mL) was added dropwise and the resulting solution was stirred for 3 hours. The contents were poured into water (40 mL) and acidified using 2.4 N HCl to pH around 1 and extracted with EtOAc (2×40 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil which was subject to flash chromatography (silica gel) and eluted with 0-100% EtOAc/hexanes to give yellow solid (0.84 g, 71%). GCMS m/z 302.0 (M+). LCMS m/z 303.0 (M+H). 1H NMR (CDCl3/400 MHz) 7.59 (s, 1H), 6.60 (s, 1H), 6.51 (s, 1H), 5.64 (q, 1H, J=7.0 Hz), 4.28 (m, 2H), 2.17 (s, 3H), 1.31 (m, 3H).

Workup

  1. additionwas added dropwise
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe combined extracts were washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil which
  8. washeluted with 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-f9af465a280442c1a922b80e56513c1e
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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