Tetrahydrofuran → HCID 21915845, compound

HRID 1628365Notes

Reaction equation

HRID 1628365 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]=O)[CH:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCl>[CH:13]([C:11]1[CH:10]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=1)=[CH2:21]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 16752340HCID 16752340, compound

Product 1

HCID 21915845HCID 21915845, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.33 g (0.01289 mol) of [1,1′;3′,1″]terphenyl-5′-carbaldehyde are dissolved in 12 ml of THF and added to methyltriphenylphosphonium bromide solution. The yellowish mixture is stirred at 0° C. for 1 h. After cooling to room temperature, the mixture is taken up in dichloromethane. The solution is washed with water, and the combined organic phases are dried over sodium sulfate. The mixture is evaporated to dryness. Column chromatography is carried out with hexane/ethyl acetate. The column chromatography results in a yield of 2.4 g (71%) of clean substance.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe solution is washed with water
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. customThe mixture is evaporated to dryness
  5. customThe column chromatography results in a yield of 2.4 g (71%) of clean substance

Sources & evidence

ORD record
ord-1ca1f472406441cdb24fcfa57bafc9e6
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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