2-Phenylethanol → HCID 10087609, compound

HRID 272802Notes

Reaction equation

HRID 272802 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([OH:15])[CH:9]=2)=[O:4].[C:17]1([CH2:23][CH2:24]O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[CH:9]=[C:10]([O:15][CH2:24][CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[CH:14]=1)=[O:4]

Participants

6

Reactant 4

HCID 60542-PhenylethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5416969Methyl 7-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate

Product 1

HCID 10087609HCID 10087609, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-hydroxyl-3-coumarin carboxylic acid methyl ester (0.6g, 3 mmol) and 2-phenyl ethanol (0.36 mL, 3 mmol) are dissolved in anhydrous tetrahydrofuran (60 mL). Triphenylphosphine (1.2 g, 4.5 mmol) is added, and diethyl azodicarboxylate (0.72 mL, 4.5 mmol) is added dropwise and slowly at 0° C. The resulting solution is stirred for 24 hours at room temperature. After the solvent was removed under reduced pressure, the residue is diluted with methanol and a white solid is separated out. The solid is recrystallized with methanol to give 0.45 g of the captioned compound, yield: 46.3%. m.p. 100-101° C. 1H NMR(CDCl3): δ=3.12(t, J=6.8 Hz, 2H), 3.92(s, 3H), 4.14(t, J=7.1 Hz, 2H), 6.79(d, J=2.4 Hz, 1H), 6.88(dd, J=2.4 Hz, 8.8 Hz, 1H), 7.21-7.35(m, 5H), 7.47(d, J=8.7 Hz, 1H), 8.50(s, 1H); Element Anyalysis, C19H16O5 (324): Calculated C, 70.37; H, 4.94. Found C, 70.25; H, 4.93; IR(KBr) :3045.1, 2952.5, 1751.1, 1693.2, 1610.3, 1554.4, 1506.2, 1436.7, 1375, 1307.5, 1222.7, 1114.7, 1018.2, 835, 749.5, 738.6, 700, 594 cm−1; EI-MS(m/z): 324(24, M+), 105(100).

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. additionthe residue is diluted with methanol
  3. customa white solid is separated out
  4. customThe solid is recrystallized with methanol

Sources & evidence

ORD record
ord-cf618d31fbd34afb8600c9cbbdb9b26e
Source dataset
uspto-grants-2008_11
Patent number
US07456205B2

Reaction notes

Loading…