Water → HCID 44579076, compound

HRID 1925089Notes

Reaction equation

HRID 1925089 reaction equation
[CH:1]([C:3]1[C:8]([C:9]2[C:10]([CH:18]=[O:19])=[CH:11][C:12]3[O:16][CH2:15][O:14][C:13]=3[CH:17]=2)=[C:7]([O:20][CH3:21])[C:6]([O:22][CH3:23])=[C:5]([O:24][CH3:25])[CH:4]=1)=[O:2].[BH4-].[Na+].O.C(OCC)(=O)C>CO>[OH:2][CH2:1][C:3]1[C:8]([C:9]2[C:10]([CH2:18][OH:19])=[CH:11][C:12]3[O:16][CH2:15][O:14][C:13]=3[CH:17]=2)=[C:7]([O:20][CH3:21])[C:6]([O:22][CH3:23])=[C:5]([O:24][CH3:25])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 372641HCID 372641, compoundHCID 4311764Sodium borohydride

Product 1

HCID 44579076HCID 44579076, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude 6-(6-formyl-2,3,4-trimethoxyphenyl)benzo[d][1,3]dioxole-5-carbaldehyde (265 mg, 0.77 mmol) in methanol (7 mL) was added sodium borohydride (80 mg, 2.1 mmol) and the solution was stirred at room temperature for 1 hour. Water (30 mL) and ethyl acetate (30 mL) were then added to the reaction, the layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined extracts were dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (40 g), eluting with hexane-ethyl acetate (1:2), followed by crystallisation (ethyl acetate), which yielded (6-(6-(hydroxymethyl)-2,3,4-trimethoxyphenyl)benzo[d][1,3]dioxol-5-yl)methanol as a white solid (230 mg, 86%); m.p. 123-124° C.; High Resolution Mass Spectrometry Found: M+Na+ 371.1105 (C18H20O7Na requires 371.1107); NMR Spectrum δH (300 MHz, CDCl3) 7.00 (2H, s, 7-H), 6.88 (1H, s, 4-H), 6.63 (1H, s, 5′-H), 6.04 (2H, s, 2-H), 4.30 (2H, m, CH2OH), 4.21 (2H, m, CH2OH), 3.93 (3H, s, OCH3), 3.91 (3H, s, OCH3), 3.62 (3H, s, OCH3); NMR Spectrum δC (75 MHz, CDCl3) 56.4, 61.4, 61.5 (CH2), 63.1 (CH2), 63.7, 101.7, 108.7, 110.4, 110.6, 126.6, 129.1, 133.8, 135.5, 142.0, 147.5, 147.8, 151.4, 153.5; νmax/cm−1 (thin film) 3254, 2944, 2889, 1603, 1480, 1410, 1328, 1235, 1146, 1111, 1033, 928; m/z (ES) 412 (MNa2H2O+, 100%), 371 (MNa+, 60); Rf(hexane-ethyl acetate 1:2) 0.14.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography over silica gel (40 g)
  7. washeluting with hexane-ethyl acetate (1:2)
  8. customfollowed by crystallisation (ethyl acetate), which

Sources & evidence

ORD record
ord-7d2c1189b9f54191985439b087ad3290
Source dataset
uspto-grants-2012_05
Patent number
US08178578B2

Reaction notes

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