Phenol → HCID 70676150, compound

HRID 2271494Notes

Reaction equation

HRID 2271494 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:16](O)[CH:17]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[Cl:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:17]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594467411-Azetidinecarboxylic acid, 3-[(3,4-dichlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 70676150HCID 70676150, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenol (0.1 mL, 0.903 mmol) was added to 10 mL of tertiary butyl 3-((3,4-dichlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate (150 mg, 0.452 mmol) and triphenylphosphine (237 mg, 0.903 mmol) dissolved in distilled tetrahydrofuran solution, and diisopropyl azocarboxylate (0.18 mL, 0.903 mmol) was slowly added at 0° C., and the mixture was stirred at room temperature for one day. The solvent of the reaction mixture was removed by reduced pressure evaporation to obtain a yellow liquid, which was purified by flash chromatography (n-hexane:ethyl acetate (4:1, v/v)). The product was identified as a single compound by TLC (n-hexane:ethyl acetate (4:1, v/v)).

Workup

  1. customThe solvent of the reaction mixture was removed by reduced pressure evaporation
  2. customto obtain a yellow liquid, which
  3. customwas purified by flash chromatography (n-hexane:ethyl acetate (4:1

Sources & evidence

ORD record
ord-9552d7f8024b4955a44b784cb9eb84eb
Source dataset
uspto-grants-2015_09
Patent number
US09120771B2

Reaction notes

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