HCID 67519252, compound → HCID 24959802, compound

HRID 1925093Notes

Reaction equation

HRID 1925093 reaction equation
[P:1]([O:35]CC1C=CC=CC=1)([O:27]CC1C=CC=CC=1)([O:3][C:4]1[C:9]2[CH2:10][O:11][CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[C:14]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[O:25][CH3:26])=[O:2]>CO.[Pd]>[P:1]([OH:35])([OH:27])([O:3][C:4]1[C:9]2[CH2:10][O:11][CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[C:14]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[O:25][CH3:26])=[O:2]

Participants

4

Reactant 1

HCID 67519252HCID 67519252, compound

Product 1

HCID 24959802HCID 24959802, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,9,10,11-Tetramethoxy-5,7-dihydrodibenzo[c,e]oxepin-4-yl bis(phenylmethyl) phosphate (39.4 mg, 0.067 mmol) in methanol (3 mL) was stirred with palladium on charcoal (10% w/w; 4 mg) under hydrogen for 2 hours at room temperature and pressure until TLC indicated the consumption of the starting material. The mixture was then passed through a small silica plug (0.5 cm depth in a Pasteur pipette) and concentrated to afford 3,9,10,11-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepin-4-yl dihydrogen phosphate as a white crystalline solid (26.6 mg, 97%); m.p. 132° C.; High Resolution Mass Spectrometry Found: M+Na+ 435.0826 (C18H21O9PNa requires 435.0821); νmax/cm−1 (thin film) 2930, 2858, 1590, 1107; NMR Spectrum δH (400 MHz, CD3OD) 3.56 (3H, s, OCH3), 3.74 (3H, s, OCH3), 3.76 (3H, s, OCH3), 3.87 (3H, s, OCH3), 3.82-3.87 (1H, m, 5-H or 7-H), 3.90-3.95 (1H, m, 5-H or 7-H), 4.34 (1H, apparent d, J 9.6 Hz, 5-H or 7-H), 5.12 (1H, apparent d, J 9.6 Hz, 5-H or 7-H), 6.86 (1H, s, 8-H), 7.12 (1H, d, J 8.7 Hz, 2-H), 7.42 (1H, br d, J 8.7 Hz, 1-H); NMR Spectrum δC (100 MHz, CD3OD) 56.94, 57.01, 61.43, 61.72, 61.86, 68.82, 101.28, 110.55, 113.71, 127.80, 128.05, 129.71, 131.78, 132.69, 144.52, 152.19, 154.90; NMR Spectrum δP (160 MHz, CD3OD)-3.52 (P); m/z (ES) 435 (MNa+, 80%).

Workup

  1. customthe consumption of the starting material
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-02f867138ae24edfb74b58ddb476b236
Source dataset
uspto-grants-2012_05
Patent number
US08178578B2

Reaction notes

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