Carbon Tetrachloride → HCID 57696849, compound

HRID 217625Notes

Reaction equation

HRID 217625 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:17]2[C@@:13]([CH3:26])([C@@H:14]([C@:18]([OH:25])([CH3:24])[CH2:19][C:20](=[CH2:23])[CH2:21]O)[CH2:15][CH2:16]2)[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:47]>CC#N>[Cl:47][CH2:21][C:20](=[CH2:23])[CH2:19][C@@:18]([C@@H:14]1[C@:13]2([CH3:26])[C@H:17]([C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][CH2:11][CH2:12]2)[CH2:16][CH2:15]1)([OH:25])[CH3:24]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57696848HCID 57696848, compound

Product 1

HCID 57696849HCID 57696849, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8 (82 mg, 0.2 mmol), Ph3P (85 mg, 3.32 mmol), CCl4 (54 mg, 0.35 mmol, dried with CaCl2), and CH3CN (2 mL, dried with CaH2) was stirred for 30 min under argon. The mixture was flash chromatographed (SiO2, 2.5×5 cm. 5% EtOAc-hexanes) to give 9 (70 mg, 77%). This unstable compound was immediately used in the next step.

Workup

  1. customchromatographed (SiO2, 2.5×5 cm. 5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-001493204e2741b1b9003aa23b135c4b
Source dataset
uspto-grants-2012_06
Patent number
US08198263B2

Reaction notes

Loading…