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

HRID 1873305Notes

Reaction equation

HRID 1873305 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][O:9]2)=[CH:4][C:3]=1[OH:13].[CH2:14]([CH:17]1[CH2:22][CH2:21][CH:20]([CH:23](O)[C:24]#[CH:25])[CH2:19][CH2:18]1)[CH2:15][CH3:16].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][CH2:8][O:9]2)=[CH:4][C:3]=1[O:13][CH:14]([CH:17]1[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:21][CH2:22]1)[C:15]#[CH:16]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 581519331-(4-Propylcyclohexyl)prop-2-yn-1-olHCID 592152417,8-Difluorochroman-6-ol

Product 1

HCID 581519137,8-Difluoro-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (26.9 mmol) of 7,8-difluorochroman-6-ol are initially introduced in 65 ml of THF together with 5.33 g (29.6 mmol) of 1-(4-propylcyclohexyl)-prop-2-yn-1-ol and 8.45 g (32.2 mmol) of triphenylphosphine, and 6.79 ml (34.9 mmol) of DIAD are added over the course of 30 min with ice-cooling. After 19 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-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-918c2e9f0685481898db33b3d2ac659d
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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