Water → 6,8-difluoro-3-[5-(6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]-2H-chromene

HRID 2420643Notes

Reaction equation

HRID 2420643 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]([CH2:15][OH:16])[CH2:13][OH:14])[O:8][CH2:7][CH:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:5]2.[F:22][C:23]1[CH:24]=[C:25]2[C:30](=[C:31]([F:33])[CH:32]=1)[O:29][CH2:28][C:27]([CH:34]=O)=[CH:26]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[F:22][C:23]1[CH:24]=[C:25]2[C:30](=[C:31]([F:33])[CH:32]=1)[O:29][CH2:28][C:27]([CH:34]1[O:16][CH2:15][CH:12]([C:11]3[CH:10]=[C:9]4[C:4]([CH2:5][CH:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:7][O:8]4)=[CH:3][C:2]=3[F:1])[CH2:13][O:14]1)=[CH:26]2

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 592883552-(6-Fluoro-3-pentylchroman-7-yl)propane-1,3-diolHCID 592883586,8-difluoro-2H-chromene-3-carbaldehyde

Product 1

HCID 592883496,8-difluoro-3-[5-(6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]-2H-chromene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.30 g (4.39 mmol) of 2-(6-fluoro-3-pentylchroman-7-yl)propane-1,3-diol and 900 mg (4.59 mmol) of 6,8-difluoro-2H-chromene-3-carbaldehyde are dissolved in 50 ml of dichloromethane and heated under reflux on a water separator for 5 h in the presence of 50 mg of p-toluenesulfonic acid. The solution is subsequently washed with sat. sodium hydrogencarbonate soln. and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is recrystallised from heptane/toluene, giving 6,8-difluoro-3-[5-(6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]-2H-chromene (trans:cis=80:20) as a colourless solid.

Workup

  1. temperatureheated
  2. washThe solution is subsequently washed with sat. sodium hydrogencarbonate soln
  3. dry with materialand dried over sodium sulfate
  4. customThe solvent is removed in vacuo
  5. customthe residue is recrystallised from heptane/toluene

Sources & evidence

ORD record
ord-2ecfa3fc07e24b36aac9080ee5a67193
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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