Propylethinylcarbinol → 6-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman

HRID 1873313Notes

Reaction equation

HRID 1873313 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].[CH:19]#[C:20][CH:21](O)[CH2:22][CH2:23][CH3:24].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>C1COCC1.O>[C:20]([CH:21]([O:18][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:12])[C:2]=1[F:1])[O:9][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:7][CH2:6]2)[CH2:22][CH2:23][CH3:24])#[CH:19]

Participants

7

Reactant 4

HCID 7746PropylethinylcarbinolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 46834772HCID 46834772, compound

Product 1

HCID 581519006-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

10.0 g (39.0 mmol) of 7,8-difluoro-2-pentylchroman-6-ol are initially introduced in 140 ml of THF together with 4.0 g (41.0 mmol) of 1-hexyn-3-ol and 11.3 g (42.9 mmol) of triphenylphosphine, and 9.1 ml (46.8 mmol) of DIAD are added over the course of 20 min with ice-cooling. After 18 h at RT, water 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 soln., and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-heptane:MTBE=2:1), giving 6-(1-ethynylbutoxy)-7,8-difluoro-2-pentylchroman as a yellow oil.

Workup

  1. additionare added over the course of 20 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 soln
  5. custom, and the solution is dried
  6. customafter removal of the solvents
  7. customis purified by column chromatography (SiO2, n-heptane:MTBE=2:1)

Sources & evidence

ORD record
ord-2fd8d632df444939aeb159f484faf82f
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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