2',4'-Dihydroxyacetophenone → HCID 9878027, compound

HRID 884426Notes

Reaction equation

HRID 884426 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[CH3:8][C:9]([C:11]1[CH:12]=[CH:13][C:14](O)=[CH:15][C:16]=1[OH:17])=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl.CCOCC>[OH:17][C:16]1[CH:15]=[C:14]([O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:13]=[CH:12][C:11]=1[C:9](=[O:10])[CH3:8]

Participants

7

Reactant 4

HCID 69902',4'-DihydroxyacetophenoneHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 9878027HCID 9878027, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of tetrahydro-4H-pyran-4-ol (1.53 g, 15 mmol), 2,4-dihydroxyacetophenone (1.52 g, 10 mmol), and triphenylphosphine, polymerbound (5 g, 3 mmol P/g resin, 15 mmol) in CH2Cl2 (150 mL) was treated with diethylazodicarboxylate (2.61 g, 15 mmol) and stirred at 20° C. for 20 h. The reaction mixture was treated with ether (200 mL) and the resin was filtered off and discarded. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 25% ether in hexanes) to yield the white solid product (0.74 g, 31%).

Workup

  1. filtrationthe resin was filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 25% ether in hexanes)

Sources & evidence

ORD record
ord-1968c5c1368b4367abbbd419f5707ee6
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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