Toluene → HCID 58535762, compound

HRID 1941729Notes

Reaction equation

HRID 1941729 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([CH:11]1[O:16][C:15](=[O:17])[CH:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH:30]4[CH2:35][CH2:34][CH:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[O:32][CH2:31]4)=[C:26]([F:41])[C:25]=3[F:42])=[C:20]([F:43])[C:19]=2[F:44])[CH2:13][CH2:12]1)[CH2:9][CH3:10].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C(O)=O>[CH2:8]([CH:11]1[O:16][CH:15]([OH:17])[CH:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH:30]4[CH2:35][CH2:34][CH:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[O:32][CH2:31]4)=[C:26]([F:41])[C:25]=3[F:42])=[C:20]([F:43])[C:19]=2[F:44])[CH2:13][CH2:12]1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 58535544HCID 58535544, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 58535762HCID 58535762, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Toluene (10 ml) was added to 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(6-pentyltetrahydro-2H-pyran-3-yl)biphenyl-4-yl)tetrahydro-2H-pyran-2-one (20) (1.2 g) prepared in the first step. A diisobutylaluminum hydride-toluene solution (0.99 M; 3.49 ml) was added dropwise at −50° C. or lower, and the stirring was continued for 3 hours. The reaction mixture was poured into a 10% aqueous solution of formic acid (15 ml) to give two layers. The water layer was extracted with toluene (10 ml) twice, and the combined organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(6-pentyltetrahydro-2H-pyran-3-yl)biphenyl-4-yl)tetrahydro-2H-pyran-2-ol (21) (1.2 g) in 98% yield.

Workup

  1. customprepared in the first step
  2. customto give two layers
  3. extractionThe water layer was extracted with toluene (10 ml) twice
  4. washthe combined organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-53c7f3c408a54eac836a1c825380c516
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

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