Formic Acid → HCID 58991876, compound

HRID 2220580Notes

Reaction equation

HRID 2220580 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C@H:11]3[CH2:27][C@H:15]4[O:16][C:17]5[C:22]([F:23])=[C:21]([O:24][CH2:25][CH3:26])[CH:20]=[CH:19][C:18]=5[C@@H:14]4[CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4]CC1.C(O)=O.O>C1(C)C=CC=CC=1>[CH2:25]([O:24][C:21]1[CH:20]=[CH:19][C:18]2[C@@H:14]3[CH2:13][CH2:12][C@@H:11]([CH:8]4[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]4)[CH2:27][C@H:15]3[O:16][C:17]=2[C:22]=1[F:23])[CH3:26]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 58991883HCID 58991883, compound

Product 1

HCID 58991876HCID 58991876, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.3 g (35.3 mmol) of (±)-(3R*,4aR*,9bS*)-3-(1,4-dioxaspiro[4.5]dec-8-yl)-7-ethoxy-6-fluoro-1,2,3,4,4a,9b-hexahydrodibenzofuran are dissolved in 200 ml of toluene and stirred vigorously together with 40 ml (1.06 mol) of formic acid with addition of 1.0 ml (55.6 mmol) of water. After 18 h, the organic phase is separated off, and the formic acid is extracted with toluene. The combined organic phases are washed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution and dried using sodium sulfate. The crude product remaining after removal of the solvent is purified by column chromatography (SiO2, toluene:ethyl acetate=4:1), giving (±)-4-((3R*,4aR*,9bS*)-7-ethoxy-6-fluoro-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-yl)cyclohexanone as colourless solid.

Workup

  1. customthe organic phase is separated off
  2. extractionthe formic acid is extracted with toluene
  3. washThe combined organic phases are washed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution
  4. customdried
  5. customafter removal of the solvent
  6. customis purified by column chromatography (SiO2, toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-489d7b2d21d349d4ad846a9ccacc09bb
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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