MeOH tetrahydrofuran → HCID 69138977, compound

HRID 2371229Notes

Reaction equation

HRID 2371229 reaction equation
C([O:9][C:10]1[CH:70]=[CH:69][C:13]([C:14]([O:16][C@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][C:22]([O:36]C(=O)C4C=CC=CC=4)=[CH:23][C:24]=3[O:27]C(=O)C3C=CC=CC=3)[O:19][C@@H:18]2[C:45]2[CH:50]=[CH:49][C:48]([O:51]C(=O)C3C=CC=CC=3)=[C:47]([O:60]C(=O)C3C=CC=CC=3)[CH:46]=2)=[O:15])=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.C1COCC1.CO>[OH-].[OH-].[Pd+2].CO.C(Cl)Cl>[OH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][C@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][C:22]([OH:36])=[CH:23][C:24]=3[OH:27])[O:19][C@@H:18]2[C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[C:47]([OH:60])[CH:46]=2)=[O:15])=[CH:69][CH:70]=1

Participants

5

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 90105144HCID 90105144, compound

Product 1

HCID 69138977HCID 69138977, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

Under an H2 atmosphere, Pd(OH)2/C (20%, 100 mg) was added to a solution of 102 (200 mg, 0.23 mmol) in a solvent mixture of THF/MeOH (1:1 v/v, 20 mL). The resulting reaction mixture was stirred at r.t. under H2 for 6 h, TLC showed that the reaction was completed. The reaction mixture was filtered to remove the catalyst. The filtrate was evaporated, and the residue was rapidly purified by flash chromatograph on silica gel (10% MeOH/CH2Cl2, then 20% MeOH/CH2Cl2) to afford 11 (82 mg, 87% yield): mp 220-222° C. (decomposed); [α]D=+87.2 (c=2.0, EtOH); 1H NMR (acetone-d6, 400 MHz): δ 7.98 (d, J=8.8 Hz, 2H), 7.13 (s, 1H), 7.04 (d, J=8.8 Hz, 2H), 6.99-6.96 (m, 2H), 6.27 (d, J=2.2 Hz, 1H), 6.19 (d, J=2.2 Hz, 1H), 5.62 (dd, J=11.8, 6.3 Hz, 1H), 5.34 (d, J=6.3 Hz), 3.15 (A of ABq, J=16.5, 5.2 Hz, 1H), 3.00 (B of ABq, J=16.5, 6.4 Hz, 1H); 13C NMR (acetone-d6, 400 MHz): δ 163.3, 160.0, 155.2, 154.5, 153.6, 143.1, 129.9, 128.7, 119.6, 116.6, 113.4, 113.3, 111.8, 111.7, 96.7, 93.8, 93.0, 76.2, 67.9, 21.9; HRMS (ESI) calcd for O22H18O8Na (M+Na) 433.0899. found 433.0909.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. customThe filtrate was evaporated
  5. customthe residue was rapidly purified by flash chromatograph on silica gel (10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-9ef29228efca4b68958e4005242824b7
Source dataset
uspto-grants-2014_04
Patent number
US08710248B2

Reaction notes

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