Ethylparaben → HCID 57770570, compound

HRID 880325Notes

Reaction equation

HRID 880325 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9]C)=[O:7])=[CH:4][CH:3]=1.[O:13]1[CH2:18][CH2:17][CH:16](O)[CH2:15][CH2:14]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[O:13]1[CH2:18][CH2:17][CH:16]([O:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 57770570HCID 57770570, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of ethyl 4-hydroxybenzoate (500 mg, 3.0 mmol), tetrahydro-2H-pyran-4-ol (307.3 mg, 3.0 mmol) and PPh3 (944 mg, 3.6 mmol) in THF (15 mL) was added DEAD (627 mg, 3.6 mmol) at 0° C. The mixture was the warmed to 21° C. and stirred for 16 h. The mixture was treated with water and the organic layer was washed with brine, dried over Na2SO4, concentrated and the residue was purified by column chromatography to give the title compound (320 mg, Yield 45%). 1H NMR (CDCl3, 400 MHz): δ 7.92 (d, J=8.9 Hz, 1H), 6.75-6.94 (m, 1H), 4.44-4.59 (m, 1H), 4.28 (d, J=7.2 Hz, 2H), 3.83-4.00 (m, 2H), 3.46-3.60 (m, 2H), 1.88-2.05 (m, 2H), 1.67-1.83 (m, 2H), 1.31 (t, J=7.2 Hz, 3H).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-39fe5a91d4f54f38bad2052d4058764f
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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