Acetic Acid → HCID 57803542, compound

HRID 2102993Notes

Reaction equation

HRID 2102993 reaction equation
FC(F)(F)C(O)=O.C(O)(=O)C.[BH4-].[Na+].[CH3:14][C:15]1[C:26]([CH3:27])=[C:25]2[C:18]([CH:19](O)[C:20]3([CH2:23][O:24]2)[CH2:22][CH2:21]3)=[CH:17][C:16]=1[OH:29]>ClCCl>[CH3:14][C:15]1[C:26]([CH3:27])=[C:25]2[C:18]([CH2:19][C:20]3([CH2:23][O:24]2)[CH2:21][CH2:22]3)=[CH:17][C:16]=1[OH:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydride2×HCID 69054129HCID 69054129, compound

Product 1

HCID 57803542HCID 57803542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred ice-cold solution of trifluoroacetic acid (2 mL) and acetic acid (2 mL) was added sodium borohydride (30 mg). After stirring 10 min, a solution of 7,8-dimethyl-4H -spiro[chromene-3,1′-cyclopropane]-4,6-diol added (30 mg) in 20 mL of dichloromethane was added in one portion. Immediately thereafter, additional 20 mg of sodium borohydride was added to the solution, which was stirred for another 10 min. The mixture was partitioned with dichloromethane and water, and the organic layer was washed, dried and evaporated. The residue was purified by silica gel column eluting with 15% EtOAc in hexane to give 7,8-dimethyl-4H-spiro[chromene-3,1′-cyclopropan]-6-ol as a white solid (20 mg).

Workup

  1. additionwas added in one portion
  2. stirringwas stirred for another 10 min
  3. customThe mixture was partitioned with dichloromethane and water
  4. washthe organic layer was washed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by silica gel column
  8. washeluting with 15% EtOAc in hexane

Sources & evidence

ORD record
ord-e5175274ab344115b4672a3961d1f9fe
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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