Triphenylphosphine → (3-(4-((1,3-Dioxolan-2-yl)methyl)benzyloxy)phenyl)-(phenyl)methanone

HRID 332655

Reaction equation

HRID 332655 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.O[C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][CH:29]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:25]2[CH:26]=[C:21]([C:19]([C:18]3[CH:27]=[CH:28][CH:29]=[CH:16][CH:17]=3)=[O:20])[CH:22]=[CH:23][CH:24]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 830503-HydroxybenzophenoneHCID 86676898(4-((1,3-Dioxolan-2-yl)methyl)phenyl)methanol

Product 1

HCID 71113108(3-(4-((1,3-Dioxolan-2-yl)methyl)benzyloxy)phenyl)-(phenyl)methanoneYield 117.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) solution of (4-((1,3-dioxolan-2-yl)methyl)phenyl)methanol (0.45 g, 2.317 mmol), 3-hydroxybenzophenone (0.551 g, 2.78 mmol) and triphenylphosphine (0.729 g, 2.78 mmol) in anhydrous THF, di-iso-propylazodicarboxylate (1.027 mL, 2.78 mmol) was added dropwise. The reaction mixture was allowed to warm to RT and stirred at this temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with 10% aqueous potassium carbonate, brine and dried (magnesium sulfate). The suspension was filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 25% ethyl acetate in iso-hexane to afford the title compound (1.022 g, >100%).

Workup

  1. additionwas added dropwise
  2. washwashed with 10% aqueous potassium carbonate, brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationThe suspension was filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 100% iso-hexane to 25% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-25d0f516749b4f2e97a0a4f49ecfd867
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Linked notes

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