MeOH tetrahydrofuran → HCID 69138977, compound

HRID 217537Notes

Reaction equation

HRID 217537 reaction equation
C([O:8][C:9]1[CH:65]=[CH:64][C:12]([C:13]([O:15][C@H:16]2[CH2:25][C:24]3[C:19](=[CH:20][C:21]([O:34]CC4C=CC=CC=4)=[CH:22][C:23]=3[O:26]CC3C=CC=CC=3)[O:18][C@@H:17]2[C:42]2[CH:47]=[CH:46][C:45]([O:48]CC3C=CC=CC=3)=[C:44]([O:56]CC3C=CC=CC=3)[CH:43]=2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1.CO>[OH-].[OH-].[Pd+2].CO.C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C@H:16]2[CH2:25][C:24]3[C:19](=[CH:20][C:21]([OH:34])=[CH:22][C:23]=3[OH:26])[O:18][C@@H:17]2[C:42]2[CH:47]=[CH:46][C:45]([OH:48])=[C:44]([OH:56])[CH:43]=2)=[O:14])=[CH:64][CH:65]=1

Participants

5

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 69139704HCID 69139704, 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 C22H18O8Na (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-3727b100895a46cbbaaeb9273f8aabc3
Source dataset
uspto-grants-2012_06
Patent number
US08193377B2

Reaction notes

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