Methanol → HCID 10769106, compound

HRID 1456858Notes

Reaction equation

HRID 1456858 reaction equation
N1C2C(=CC=CC=2)C=CC=1C[O:12][C:13](=O)[CH2:14][CH2:15][C:16]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]2[CH:53]=[CH:52][C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]=2)=[CH:38][CH:37]=1)([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)=[CH:20][CH:19]=1)[CH3:17].[BH4-].[Na+].CO.O>C1COCC1>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]3[CH:53]=[CH:52][C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:45]=3)=[CH:38][CH:37]=2)([CH3:17])[CH2:15][CH2:14][CH2:13][OH:12])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 54443927HCID 54443927, compound

Product 1

HCID 10769106HCID 10769106, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture in THF (50 mL) of 4.4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid 2-quinolylmethyl ester (2.1 g, 3 mmol), prepared as in Example 1, and sodium borohydride (380 mg, 10 mmol) was added dropwise methanol at 50°-55° C. and the mixture was stirred for 30 minutes. The mixture was cooled to room temperature, poured into water (50 mL) and acidified to pH 4. The resulting mixture was extracted with ethyl acetate, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (methylene chloride-ethyl acetate 3:1) to afford 1.46 g (88%) of 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentan-1-ol: 1H NMR (300 MHz, DMSO-d6) d 1.18 (m, 2H), 1.48 (s, 3H), 2.00 (m, 2H), 3.34 (m, 2H), 4.34 (t, 1H, J=6 Hz), 5.30 (s, 4H), 6.96 (d, 4H, J=9 Hz), 7.09 (d, 4H, J=9 Hz), 7.64 (m, 4H), 7.79 (m, 2H), 8.00 (t, 4H, J=8 Hz), 8.41 (d, 2H, J=8 Hz); MS (DCl--NH3) m/e 555 (M+H)+. Anal. Calc'd. for C37H34N2O3.0.5 H2O: C, 78.84; H, 6.44; N, 4.97. Found: C, 78.67; H, 5.95; N, 4.70.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (methylene chloride-ethyl acetate 3:1)

Sources & evidence

ORD record
ord-d40cc56d0e8a4140b0daa1d3008aa058
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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