1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 86630328, compound

HRID 1171926Notes

Reaction equation

HRID 1171926 reaction equation
[S:1]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)([O:4][CH2:5][CH:6]([OH:9])[CH2:7][OH:8])(=[O:3])=[O:2].[CH3:17][O:18][C:19]1[CH:40]=[CH:39][C:22]([C:23](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[S:1]([O:4][CH2:5][CH:6]([CH2:7][O:8][C:23]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:40][CH:39]=1)[OH:9])([C:10]1[CH:11]=[CH:12][C:13]([CH3:14])=[CH:15][CH:16]=1)(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 52356262,3-Dihydroxypropyl 4-methylbenzene-1-sulfonate

Product 1

HCID 86630328HCID 86630328, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

(±)-2,3-Dihydroxypropyl tosylate (IV) (525 mg, 2.13 mmol, 1 eq.) was dissolved in pyridine (20 mL, anhydrous) and cooled to 0° C. 4,4′-Dimethoxytrityl chloride (758 mg, 2.24 mmol, 1.05 eq.) was added in 3 portions over 2 h and the reaction solution was allowed to warm up to rt. After 2 h, sat. aq. NaHCO3 (75 mL) was added to the reaction mixture, followed by extraction with CH2Cl2 (3×75 mL). The extract was dried with Na2SO4, filtered, concentrated in vacuo and dried by coevaporation with toluene (3×). Purification by flash column chromatography (SiO2, 1:2:97 NEt3/Et2O/CH2Cl2) gave V as a white powder (770.6 mg, 66%). 1H NMR (300 MHz, CD2Cl2/D2O): δ=7.74 (d, J=8.4 Hz, 2H, arom.), 7.36-7.21 (m, 11H, arom.), 6.82 (d, J=5.1 Hz, 4H, arom.), 4.10-3.98 (m, 2H, CH2OTs), 3.92-3.89 (m, 1H, CHOH), 3.78 (s, 6H, OCH3), 3.13-3.11 (m, 2H, CH2ODMT), 2.44 (s, 3H, C6H4CH3); 13C{1H} NMR (75.5 MHz, CD2Cl2/D2O): δ=159.3, 145.8, 145.3, 136.1, 133.1, 130.6, 129.6, 128.44, 128.41, 127.5, 127.4, 113.7, 86.9, 71.8, 69.3, 64.1, 55.8, 22.0; MS (EI): m/z. calcd for [C31H32O7S]+: 548.1869. found: 548.1867 [M]+. elemental analysis calcd (%) for C31H32O7S: C, 67.86; H, 5.88; found: C, 67.84; H, 5.93.

Workup

  1. temperatureto warm up to rt
  2. extractionfollowed by extraction with CH2Cl2 (3×75 mL)
  3. dry with materialThe extract was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dry with materialdried by coevaporation with toluene (3×)
  7. customPurification by flash column chromatography (SiO2, 1:2:97 NEt3/Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-9f7de837824748e5b76de75f35645ef0
Source dataset
uspto-grants-2010_11
Patent number
US07829735B2

Reaction notes

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