Tetrahydrofuran → Biphenyl-4-yl 3-phenoxyacrylate

HRID 1053529Notes

Reaction equation

HRID 1053529 reaction equation
N1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])CC1.N1([CH:15]=[CH:16][C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)=[O:18])CCCCC1.[CH2:32]1COC[CH2:33]1>>[O:8]([CH:15]=[CH:16][C:17]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:24][CH:25]=1)=[O:18])[C:7]1[CH:4]=[CH:5][CH:6]=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4207714-PiperidinemethanolHCID 131736279HCID 131736279, compound

Product 1

HCID 131736282Biphenyl-4-yl 3-phenoxyacrylate

Procedure

4-Piperidinemethanol (0.06 g, 0.5 mmol) and compound 3 (0.11 g, 0.5 mmol) [4 (0.22 g, 0.5 mmol) or 5 (0.19 g, 0.5 mmol)] were dissolved in dry THF (5 mL), and the solution was stirred at room temperature for 30-45 min. The solvent was removed under reduced pressure at room temp to give the crude product which was then purified by column chromatography using ethyl acetate:hexane (7:3 or 8:3) to give compound 6 (7 or 8).

Workup

  1. customThe solvent was removed under reduced pressure at room temp
  2. customto give the crude product which
  3. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-d727b0a42c7845fc9670aa664388b319
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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