1,3-Propanediol → HCID 54404287, compound

HRID 442934Notes

Reaction equation

HRID 442934 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[S:11]([O:14][C:15]1[CH:16]=[C:17]([OH:22])[CH:18]=[C:19]([CH3:21])[CH:20]=1)(=[O:13])=[O:12].[CH2:23](O)[CH2:24][CH2:25][OH:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[S:11]([O:14][C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[O:22][CH2:23][CH2:24][CH2:25][OH:26])(=[O:12])=[O:13]

Participants

7

Reactant 5

HCID 104421,3-PropanediolHCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53850903HCID 53850903, compound

Product 1

HCID 54404287HCID 54404287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 500 mg (1.54 mmol) of 3-(2,5-dimethoxyphenylsulfonyloxy)-5-methylphenol, as prepared in the preceding step, 1.1 mL (15 mmol) of 1,3-propanediol and 808 mg (3.08 mmol) of triphenylphosphine in 12 mL of anhydrous tetrahydrofuran was added 485 mg (3.08 mmol) of diethyl azodicarboxylate dropwise over 15 min. After stirring at ambient temperature for 1 h, the reaction mixture was concentrated to a yellow syrup. The resulting mixture was flash chromatographed on 40 g of silica gel with 50-75% ethyl acetate-hexane to afford a mixture of the desired product and triphenylphosphine oxide. Chromatography on 35 g of silica gel with 4% acetone-dichloromethane afforded 483 mg (82% yield) of the title compound as a colorless resin: 1H-NMR (300 MHz; CDCl3) δ 7.34 (d, 1 H, J=3.1 Hz), 7.15 (dd, 1 H, J=9.1, 3.1 Hz), 7.03 (d, 1 H, J=9.1 Hz), 6.59 (m, 1 H), 6.53 (m, 1 H), 6.48 (t, 1 H, J=2.1 Hz), 4.01 (t, 2 H, J=6.0 Hz), 3.97 (s, 3 H), 3.81 (dd, 2 H, J=11.2, 5.8 Hz), 3.76 (s, 3 H), 2.25 (s, 3 H) and 1.98 (pentet, 2 H, J=6.0 Hz).

Workup

  1. concentrationthe reaction mixture was concentrated to a yellow syrup
  2. customchromatographed on 40 g of silica gel with 50-75% ethyl acetate-hexane
  3. customto afford

Sources & evidence

ORD record
ord-6caa99aaba684ff5b3fa0c598ebc3ca1
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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