Hydrochloric Acid → 4'-(Benzyloxy)-3'-(4,4-dimethylpent-1-en-1-yl)-2-fluoro-5-methoxy-1,1'-biphenyl

HRID 1049460Notes

Reaction equation

HRID 1049460 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[CH:11][C:10]=1[CH:24]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CS([O-])(=O)=O.[CH3:33][C:34]([CH3:57])([CH3:56])[CH2:35][CH2:36][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[CH:11][C:10]=1[CH:24]=[CH:36][CH2:35][C:34]([CH3:57])([CH3:56])[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 85243721(3,3-Dimethylbutyl)(triphenyl)phosphonium methanesulfonateHCID 1177599394-(Benzyloxy)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 1317360124'-(Benzyloxy)-3'-(4,4-dimethylpent-1-en-1-yl)-2-fluoro-5-methoxy-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(benzyloxy)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-3-carbaldehyde (1.40 g) in THF (10 mL) was added 60% sodium hydride (240 mg) at room temperature, and the mixture was stirred for 30 min. To the reaction mixture was added dropwise a solution of (3,3-dimethylbutyl) (triphenyl)phosphonium methanesulfonate (1.70 g) in THF (10 mL), and the mixture was stirred at 50° C. for 1 hr. 1N Hydrochloric acid was added 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 to give a crude product. This compound was used for the net step without further purification.

Workup

  1. stirringthe mixture was stirred at 50° C. for 1 hr
  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

Sources & evidence

ORD record
ord-00142b1197db4194aa9d726849620cf9
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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