2-Phenylethanol → HCID 68843385, compound

HRID 660513Notes

Reaction equation

HRID 660513 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30](O)[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:21])(=[O:22])[N:19]([CH2:23][CH2:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 60542-PhenylethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68842563HCID 68842563, compound

Product 1

HCID 68843385HCID 68843385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(2-benzyloxy-4-hydroxyphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (90 mg, 0.21 mmol), phenethyl alcohol (37.9 mg, 0.31 mmol), DIAD (0.0612 mL, 0.31 mmol), and triphenylphosphine (81.5 mg, 0.31 mmol) in (THF 5 mL) is stirred at RT for 18 h. The solvent is removed under reduced pressure and the residue chromatographed on a Biotage 40S column using a gradient of 80:20 to 60:40 hexane/EtOAc as eluent to afford the title compound: 1H NMR (CDCl3δ7.30 (m, 11H), 6.62 (d, J=2.8 Hz, 1H), 6.43 (dd, J=8.6, 2.8 Hz, 1H), 5.00 (s, 2H), 4.25 (s, 2H), 4.11 (t, J=7.1 Hz, 2H), 3.51 (m, 2H), 3.03 (t, J=7.1 Hz, 2H), 0.99 (m, 2H), 0.00 (s, 9H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue chromatographed on a Biotage 40S column

Sources & evidence

ORD record
ord-b576463c541b460eb7c9aa893f8c3934
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…