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Water → 1-(4'-Trifluoromethyl-biphenyl-4-yl)-heptan-1-ol

HRID 1669333
Notes
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Reaction equation

HRID 1669333 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:9][C:10]([F:26])([F:25])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.O.[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:9][C:10]([F:25])([F:26])[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]([OH:24])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:19][CH:18]=2)=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehydeHCID 178444609HCID 178444609, compound

Product 1

HCID 597294131-(4'-Trifluoromethyl-biphenyl-4-yl)-heptan-1-olYield 73%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

Add hexyl magnesium bromide (2.0M in ethyl ether, 8 mL, 16 mmol) to 4′-trifluoromethyl-biphenyl-4-carbaldehyde (2.0 g, 8 mmol) (prepared in a manner substantially similar to preparation 25, or other methods known in the art) in tetrahydro-furan (30 mL) at 0° C. under inert atmosphere. Stir 1.5 hours. Quench reaction with saturated solution of ammonium chloride, dilute with ethyl acetate. Wash organic phase with water then saturated sodium chloride solution. Dry organic fraction with Na2SO4, filter, and concentrate under reduced pressure. Purify on silica gel chromatography (0-30% Ethyl acetate/hexanes gradient) to provide 1.95 g of title compound (73%).

Workup

  1. customprepared in a manner substantially similar to preparation 25, or other methods
  2. customat 0° C.
  3. customQuench
  4. customreaction with saturated solution of ammonium chloride
  5. filtrationDry organic fraction with Na2SO4, filter
  6. concentrationconcentrate under reduced pressure
  7. customPurify on silica gel chromatography (0-30% Ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-d8c67ec133334ab4a89ec726ce5197cb
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989457B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes