7-Ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene → 8-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-3H-benzo[f]chromene

HRID 1873325Notes

Reaction equation

HRID 1873325 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([O:16][CH:17]([CH:20]3[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]3)[C:18]#[CH:19])[C:10]([F:15])=[C:11]2[F:14])=[CH:6][CH:5]=1)[CH3:2]>C(N(CC)C1C=CC=CC=1)C.CC(OC)(C)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH:19]=[CH:18][CH:17]([CH:20]4[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]4)[O:16][C:9]=3[C:10]([F:15])=[C:11]([F:14])[C:12]=2[CH:13]=1)[CH3:2]

Participants

4

Reactant 1

HCID 581518997-Ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene

Product 1

HCID 581518988-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-3H-benzo[f]chromene

Reagents, catalysts & solvents 2

HCID 7061N,N-DiethylanilineSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

7.75 g (about 18.6 mmol) of 7-ethoxy-1,2-difluoro-3-[1-(4-propylcyclohexyl)prop-2-ynyloxy]naphthalene are heated at 205° C. for 4.5 h in 80 ml of N,N-diethylaniline. The batch is diluted with MTBE and washed a number of times with hydrochloric acid. The organic phase is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1). The further purification is carried out by recrystallisation from n-heptane, giving 8-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-3H-benzo[f]chromene as a yellow solid.

Workup

  1. washwashed a number of times with hydrochloric acid
  2. customThe organic phase is dried
  3. customevaporated to dryness
  4. customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1)
  5. customThe further purification
  6. customis carried out by recrystallisation from n-heptane

Sources & evidence

ORD record
ord-cb272f2a154641a290b0f320701a0725
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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