Water → HCID 16749114, compound

HRID 901160Notes

Reaction equation

HRID 901160 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH2:21]O)=[CH:15][C:14]=1[Cl:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(OCC)C.O>ClCCl>[CH2:5]([O:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH2:21][Cl:3])=[CH:15][C:14]=1[Cl:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 896963HCID 896963, compound

Product 1

HCID 16749114HCID 16749114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2 mL) was added to solution of (4-benzyloxy-3-chloro-5-methoxy-phenyl)-methanol (CAB02170, 2.703 g, 9.7 mmol) in dichloromethane (10 mL). The solution was stirred for 1 h at room temperature, then diethyl ether (50 mL) and water (20 mL) were added. The organic layer was separated, washed with conc. sodium bicarbonate solution (10 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in dichloromethane (5 mL) and precipitated by addition of hexane (ca. 50 mL). Yield: 2.730 g (95%) white powder. 1H-NMR (400 MHz, CDCl3) δ=3.89 (s, 3H, —OCH3), 4.52 (s,2H), 5.07 (s, 2H), 6.87 (d, J=2.0 Hz, 1H), 7.03 (d, J=2.0 Hz, 1H), 7.33-7.43 (m, 3H), 7.53-7.58 (m, 2H). LRMS (FAB+): 91.0 (100), 296.0 (17, M+H]+).

Workup

  1. customThe organic layer was separated
  2. washwashed with conc. sodium bicarbonate solution (10 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  6. customprecipitated by addition of hexane (ca. 50 mL)

Sources & evidence

ORD record
ord-c89c894383e94be7b6629aa2fdd5cb73
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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