Propylethinylcarbinol → HCID 58151944, compound

HRID 1873317Notes

Reaction equation

HRID 1873317 reaction equation
[F:1][C:2]1[C:3]([OH:22])=[CH:4][C:5]2[CH2:6][CH2:7][CH:8]([CH:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]3)[CH2:9][C:10]=2[C:11]=1[F:12].[CH:23]#[C:24][CH:25](O)[CH2:26][CH2:27][CH3:28].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:24]([CH:25]([O:22][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:12])[C:2]=1[F:1])[CH2:9][CH:8]([CH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]1)[CH2:7][CH2:6]2)[CH2:26][CH2:27][CH3:28])#[CH:23]

Participants

7

Reactant 4

HCID 7746PropylethinylcarbinolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58151935HCID 58151935, compound

Product 1

HCID 58151944HCID 58151944, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7.0 g (22.7 mmol) of 3,4-difluoro-6-(4-propylcyclohexyl)-5,6,7,8-tetrahydronaphthalen-2-ol are initially introduced in 90 ml of THF together with 2.70 ml (24.0 mmol) of 1-hexyn-3-ol and 6.60 g (25.2 mmol) of triphenylphosphine. 5.3 ml (46.8 mmol) of DIAD in 10 ml of THF are added over the course of 20 min with ice-cooling. After 19 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-(4-propylcyclohexyl)-1,2,3,4-tetrahydronaphthalene as a colourless solid.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted a number of times with MTBE
  3. washThe combined organic phases are washed with water and saturated sodium chloride soln
  4. custom, and the solution is dried
  5. customafter removal of the solvents
  6. customis purified by column chromatography (SiO2, n-heptane MTBE=2:1)

Sources & evidence

ORD record
ord-95d931fc16054e5aac801142223e3b46
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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