Hydrochloric Acid → HCID 42604745, compound

HRID 2220581Notes

Reaction equation

HRID 2220581 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([O:9][C:10]1[CH:30]=[CH:29][C:13]2[C@@H:14]3[CH2:20][CH2:19][C@@H:18]([CH:21]4[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]4)[CH2:17][C@H:15]3[O:16][C:12]=2[C:11]=1[F:31])[CH3:8].O.Cl>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]([O:9][C:10]1[CH:30]=[CH:29][C:13]2[C@@H:14]3[CH2:20][CH2:19][C@@H:18]([CH:21]4[CH2:22][CH2:23][CH:24]([CH:27]=[CH2:1])[CH2:25][CH2:26]4)[CH2:17][C@H:15]3[O:16][C:12]=2[C:11]=1[F:31])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 42604744HCID 42604744, compound

Product 1

HCID 42604745HCID 42604745, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

9.65 g (27.0 mmol) of methyltriphenylphosphonium bromide are initially introduced in 100 ml of THF, and 3.09 g (27.0 mmol) of potassium tert-butoxide in 60 ml of THF are added at −5° C. After 1 h at this temperature, 8.40 g (about 24 mmol) of crude (±)-4-((3R*,4aR*,9bS*)-7-ethoxy-6-fluoro-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-yl)cyclohexanecarbaldehyde as a solution in 90 ml of THF are added dropwise, and the batch is stirred at room temperature for 3 h. The reaction solution is hydrolysed using water and acidified using 2 N HCl. The mixture is extracted with MTBE, and the combined organic phases are dried using sodium sulfate. The crude product remaining after removal of the solvents is filtered adsorptively (SiO2, toluene), and the filtrate is concentrated to dryness. Repeated recrystallisation of the residue from ethanol gives (±)-(3R*,4aR*,9bS*)-7-ethoxy-6-fluoro-3-(4-vinylcyclohexyl)-1,2,3,4,4a,9b-hexahydrodibenzofuran as colourless solid (m.p. 132° C.).

Workup

  1. extractionThe mixture is extracted with MTBE
  2. customthe combined organic phases are dried
  3. customafter removal of the solvents
  4. filtrationis filtered adsorptively (SiO2, toluene)
  5. concentrationthe filtrate is concentrated to dryness
  6. customrecrystallisation of the residue from ethanol

Sources & evidence

ORD record
ord-46615591226b476c879539c589778d66
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

Loading…