Hydrochloric Acid → HCID 86698464, compound

HRID 527678Notes

Reaction equation

HRID 527678 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[O:11][CH2:12][CH2:13][C:14]3([CH2:16][CH2:15]3)[C:6]=12.Cl.O>CO>[C:14]12([C:6]3[C:5]([OH:4])=[CH:10][CH:9]=[CH:8][C:7]=3[O:11][CH2:12][CH2:13]1)[CH2:16][CH2:15]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 67966806HCID 67966806, compound2×

Product 1

HCID 86698464HCID 86698464, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

5-{[(methyloxy)methyl]oxy}-2,3-dihydrospiro[chromene-4,1′-cyclopropane] (Intermediate 220, 145 mg, 0.658 mmol) was dissolved in MeOH (6.0 mL) and a 2N aqueous solution of HCl (0.494 mL, 0.99 mmol) was added and the reaction mixture was stirred at 50° C. overnight. After addition of water, MeOH was removed under vacuum and the aqueous phase was extracted with ethyl acetate (three times). Combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (Biotage system) on silica gel using cyclohexane to cyclohexane/ethyl acetate 9:1 as eluents affording the title compound (64 mg).

Workup

  1. customwas removed under vacuum
  2. extractionthe aqueous phase was extracted with ethyl acetate (three times)
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (Biotage system) on silica gel

Sources & evidence

ORD record
ord-f1f0a90e06a24d748a6da69769a9091b
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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