Triphenylphosphine → HCID 58437603, compound

HRID 2092374Notes

Reaction equation

HRID 2092374 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2].[CH3:16][C@H:17](O)[CH2:18][CH3:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C@@H:17]([CH2:18][CH3:19])[CH3:16])=[C:8]([O:13][CH3:14])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 108965Ethyl homovanillateHCID 444683(+)-2-Butanol

Product 1

HCID 58437603HCID 58437603, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester (700 mg, 3.33 mmol) in DCM (40 ml) were successively added (S)-butan-2-ol (0.37 ml, 4.0 mmol), supported PPh3 (loading of 1.52 mmol/g, 4.38 g, 6.66 mmol) and DTAD (1.15 g, 5.0 mmol). The reaction mixture was shaken at RT for 3 h, then filtered and the resin was washed with DCM. The filtrate was evaporated to dryness and the resulting residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/TBME 95:5→1:1) to yield the title compound (818 mg, 3.07 mmol, 92%) as a colorless oil. TLC: RF=0.85 (heptane/DCM/TBME 1:1:2); HPLC: BtRet=2.46 min; API-MS: m/z 267.2 [M+H]+; 1H NMR (400 MHz, CDCl3): 1.00 (t, J=7.5, 3H), 1.28 (t, J=7.1, 3H), 1.33 (d, J=6.1, 3H), 1.60-1.70 (m, 1H), 1.77-1.89 (m, 1H), 3.56 (s, 2H), 3.86 (s, 3H), 4.17 (q, J=7.1, 2H), 4.25 (sxt, J=6.1, 1H), 6.79 (dd, J=8.3, 2.0, 1H), 6.83-6.87 (m, 2H).

Workup

  1. filtrationfiltered
  2. washthe resin was washed with DCM
  3. customThe filtrate was evaporated to dryness
  4. customthe resulting residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/TBME 95:5→1:1)

Sources & evidence

ORD record
ord-41fbae0c6fd547e1a2a8b2ecaccb1f7f
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

Loading…