Hydrochloric Acid → 1-(4-(Benzyloxy)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-3-yl)-3,3-dimethylbutan-1-ol

HRID 1049440Notes

Reaction equation

HRID 1049440 reaction equation
FC1C=CC(OC)=CC=1C1C=CC(O[Si](C(C)C)(C(C)C)C(C)C)=CC=1[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29].[CH2:32]([O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[CH:48][C:47]=2[F:54])=[CH:42][C:41]=1[CH:55]=[O:56])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>C(OCC)C.C1COCC1>[CH2:32]([O:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[CH:48][C:47]=2[F:54])=[CH:42][C:41]=1[CH:55]([OH:56])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1177599394-(Benzyloxy)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-3-carbaldehydeHCID 131736007((2'-Fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)oxy)triisopropylsilane

Product 1

HCID 1177597441-(4-(Benzyloxy)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-3-yl)-3,3-dimethylbutan-1-olYield 103.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of neopentylmagnesium bromide (2.00 g) prepared in Example 2, step F, in diethyl ether (10 mL) was added dropwise to a mixed solution of 4-(benzyloxy)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-3-carbaldehyde (2.00 g) in THF (10 mL) and diethyl ether (10 mL) at room temperature, and the mixture was stirred at 40° C. for 1 hr. The reaction mixture was cooled to room temperature, 1N hydrochloric acid was added dropwise, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.90 g) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d3c2315e8c034e8bbb34a1ddd310eef0
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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