Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 131734416, compound

HRID 587863Notes

Reaction equation

HRID 587863 reaction equation
[C:1]12([O:16][CH2:15][CH2:14][O:13]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][C@@H:3]([CH:11]=O)[CH2:2]2.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])C=CC=CC=1>C(Cl)Cl>[C:1]12([O:16][CH2:15][CH2:14][O:13]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][C@@H:3]([CH:11]=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:2]2

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 118324708HCID 118324708, compound

Product 1

HCID 131734416HCID 131734416, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of (R)-3′,4′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-naphthalene]-3′-carbaldehyde (4.1 g, 18.79 mmol) in DCM (10 mL), ethyl 2-(triphenyl phosphoranylidene)acetate (7.85 g, 22.54 mmol) was added and reaction mixture was stirred at RT for 16 h. After completion of reaction, reaction mixture was concentrated under vacuum to get 5.5 g of crude compound. This crude compound was further purified by flash chromatography (Biotage) using eluent hexane/ethyl acetate 80:20 to get the title compound (2.5 g, 46.2% yield); m/z 288.34

Workup

  1. customreaction mixture
  2. customAfter completion of reaction, reaction mixture
  3. concentrationwas concentrated under vacuum
  4. customto get 5.5 g of crude compound
  5. customThis crude compound was further purified by flash chromatography (Biotage)

Sources & evidence

ORD record
ord-e45f515da89d48d2bab69870791f80aa
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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