Diethyl Ether → HCID 9878027, compound

HRID 349677Notes

Reaction equation

HRID 349677 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.CCOCC>C(Cl)Cl>[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

6

Reactant 4

HCID 3283Diethyl EtherHCID 69902',4'-DihydroxyacetophenoneHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 9878027HCID 9878027, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 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 triphenyiphosphine, polymer-bound (5 g, 3 mmol P/g resin, 15 mmol) in CH2Cl2 (150 mL) was treated with diethyilazodicarboxylate (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 irn 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. additionwas treated with diethyilazodicarboxylate (2.61 g, 15 mmol)
  2. filtrationthe resin was filtered off
  3. concentrationThe filtrate was concentrated irn vacuo
  4. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 25% ether in hexanes)

Sources & evidence

ORD record
ord-75ab5fd187374910a1c40fbde68851bd
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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