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4-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pent-4-en-1-ol → 4-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexan-1-ol

HRID 1362524
Notes
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Reaction equation

HRID 1362524 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH:20][CH3:21])[CH2:11][C:12]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH2:13][OH:14])=[C:6]([O:22][CH3:23])[CH:5]=1)([CH3:3])[CH3:2].C(C1C=CC(C(=C)C(C)C(O)(C(F)(F)F)CO)=C(OC)C=1)(C)C>C(O)C.[Pd].[C]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:20][CH3:21])[CH2:11][C:12]([OH:19])([C:15]([F:17])([F:16])[F:18])[CH2:13][OH:14])=[C:6]([O:22][CH3:23])[CH:5]=1)([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 669694954-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pent-4-en-1-olHCID 66969593HCID 66969593, compound

Product 1

HCID 669694324-(4-Isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexan-1-ol

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702Ethanol
Solvent

Procedure

The mixture of 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)-hex-4-en-1-ol and 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pent-4-en-1-ol (4.6 g, 13.84 mmol) is dissolved in ethanol (100 ml). Following addition of 10% Pd/carbon (0.7 g) hydrogen is introduced into the reaction mixture for four hours via a balloon. The catalyst is filtered off with suction (glass fibre filter) and the precipitate is washed with ethanol. Following removal of the solvent on a rotary evaporator, the residue (4.59 g, 99.2%) is used in crude form in the next step. It consists of a mixture of 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexan-1-ol and 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pentan-1-ol (ratio 30:70).

Workup

  1. additionis introduced into the reaction mixture for four hours via a balloon
  2. filtrationThe catalyst is filtered off with suction (glass fibre filter)
  3. washthe precipitate is washed with ethanol
  4. customremoval of the solvent
  5. customon a rotary evaporator
  6. additionIt consists of a mixture of 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexan-1-ol and 4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pentan-1-ol (ratio 30:70)

Sources & evidence

ORD record
ord-c78776ca6cb64343a8fd373b351b1f36
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07880042B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes