Sodium Chloride → 7,8-Difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

HRID 1873311Notes

Reaction equation

HRID 1873311 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[OH:18].[CH2:19]([CH:22]1[CH2:27][CH2:26][CH:25]([CH:28](O)[C:29]#[CH:30])[CH2:24][CH2:23]1)[CH2:20][CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl-].[Na+]>C1COCC1>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[O:18][CH:19]([CH:22]1[CH2:23][CH2:24][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:26][CH2:27]1)[C:20]#[CH:21]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 46834772HCID 46834772, compoundHCID 581519331-(4-Propylcyclohexyl)prop-2-yn-1-ol

Product 1

HCID 581519077,8-Difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.0 g (31.2 mmol) of 7,8-difluoro-2-pentylchroman-6-ol are initially introduced in 75 ml of THF together with 6.75 g (37.4 mmol) of 1-(4-propylcyclohexyl)prop-2-yn-1-ol and 9.83 g (37.6 mmol) of triphenylphosphine, and 7.89 ml (40.6 mmol) of DIAD are added over the course of 30 min with ice-cooling. After 20 h at RT, semi-saturated sodium chloride solution is added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and saturated sodium chloride solution, and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-pentane:MTBE=2:1), giving 7,8-difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman as a pale-brown oil.

Workup

  1. additionare added over the course of 30 min with ice-
  2. temperaturecooling
  3. extractionthe mixture is extracted a number of times with MTBE
  4. washThe combined organic phases are washed with water and saturated sodium chloride solution
  5. customthe solution is dried
  6. customafter removal of the solvents
  7. customis purified by column chromatography (SiO2, n-pentane:MTBE=2:1)

Sources & evidence

ORD record
ord-ebb990bc988347989bde908591a0fd3b
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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