Hydrochloric Acid → HCID 58151924, compound

HRID 1873318Notes

Reaction equation

HRID 1873318 reaction equation
[C:1]([CH:3]([O:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([F:19])[C:17]=1[F:18])[CH2:14][CH:13]([CH:20]1[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]1)[CH2:12][CH2:11]2)[CH2:4][CH2:5][CH3:6])#[CH:2].Cl>C(N(CC)C1C=CC=CC=1)C>[F:18][C:17]1[C:8]2[O:7][CH:3]([CH2:4][CH2:5][CH3:6])[CH:1]=[CH:2][C:9]=2[C:10]2[CH2:11][CH2:12][CH:13]([CH:20]3[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]3)[CH2:14][C:15]=2[C:16]=1[F:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58151944HCID 58151944, compound

Product 1

HCID 58151924HCID 58151924, compound

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Procedure

4.5 g (11.6 mmol) of 6-(1-ethynylbutoxy)-7,8-difluoro-2-(4-propylcyclohexyl)-1,2,3,4-tetrahydronaphthalene are heated at 200° C. for 2 h in 45 ml of N,N-diethylaniline. After cooling, the batch is added to a mixture of 2 N hydrochloric acid and ice, and the mixture is extracted with MTBE. The organic phase is washed with 2 N hydrochloric acid and water, and the solution is dried using sodium sulfate. The residue remaining after removal of the solvent is purified by column chromatography (SiO2, n-heptane:toluene=9:1), giving 5,6-difluoro-3-propyl-8-(4-propylcyclohexyl)-7,8,9,10-tetrahydro-3H-benzo[f]chromene as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with MTBE
  3. washThe organic phase is washed with 2 N hydrochloric acid and water
  4. customthe solution is dried
  5. customafter removal of the solvent
  6. customis purified by column chromatography (SiO2, n-heptane:toluene=9:1)

Sources & evidence

ORD record
ord-a2df822eb9984ac0982f0f9e14205a6e
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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