Water → HCID 86698439, compound

HRID 527604Notes

Reaction equation

HRID 527604 reaction equation
COC[O:4][C:5]1[C:10]2[C:11]3([CH2:14][O:15][CH2:16][C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH2:13][CH2:12]3.O>CO>[C:11]12([C:10]3=[C:5]([OH:4])[CH:6]=[CH:7][CH:8]=[C:9]3[CH2:16][O:15][CH2:14]1)[CH2:13][CH2:12]2

Participants

4

Reactant 2

HCID 962WaterHCID 67960190HCID 67960190, compound2×

Product 1

HCID 86698439HCID 86698439, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-{[(methyloxy)methyl]oxy}-1H-spiro[2-benzopyran-4,1′-cyclopropane] (Intermediate 135, 380 mg) in methanol (10 mL) HCl 10% in water (1.048 mL, 3.45 mmol) was added and the reaction mixture was stirred overnight at 50° C. The combined solvents were evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane/ethyl acetate as eluents from 100:0 to 8:2. This afforded the title compound as a white solid (260 mg).

Workup

  1. customThe combined solvents were evaporated
  2. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a 25 g SNAP column and cyclohexane/ethyl acetate as eluents from 100:0 to 8:2

Sources & evidence

ORD record
ord-881fd9c928b344e1bf2c254e91d4e654
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…