Water → HCID 86686469, compound

HRID 513253Notes

Reaction equation

HRID 513253 reaction equation
N1C(C)=CC=CC=1C.O[C:10]1[C:11]2[C:16]([C:17]([O:25][CH3:26])=[C:18]3[C:23]=1[C:22](=[O:24])[CH2:21][CH2:20][CH2:19]3)=[CH:15][C:14]([CH3:27])=[C:13](/[CH:28]=C/C)[C:12]=2[O:31][CH2:32][O:33][CH3:34].I([O-])(=O)(=O)=[O:36].[Na+].[OH2:41]>O1CCCC1>[OH:41][C:10]1[C:23]2[C:22](=[O:24])[CH2:21][CH2:20][CH2:19][C:18]=2[C:17]([O:25][CH3:26])=[C:16]2[C:11]=1[C:12]([O:31][CH2:32][O:33][CH3:34])=[C:13]([CH:28]=[O:36])[C:14]([CH3:27])=[CH:15]2

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 86686470HCID 86686470, compound

Product 1

HCID 86686469HCID 86686469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

2,6-Lutidine (130 μL, 1.12 mmol, 2.0 equiv) was added to an ice-cooled mixture of (E)-9-hydroxy-10-methoxy-8-(methoxymethoxy)-6-methyl-7-(prop-1-enyl)-3,4-dihydroanthracen-1-one (200 mg, 0.56 mmol, 1 equiv), potassium osmate dihydrate (10 mg, 0.028 mmol, 0.05 equiv), and sodium periodate (480 mg, 2.24 mmol, 4.0 equiv) in a mixture of tetrahydrofuran (10 mL) and water (5 mL). After 10 min, the cooling bath was removed and the reaction flask was allowed to warm to 23° C. After 2.5 h, the reaction mixture was partitioned between water (50 mL) and ethyl acetate (100 mL). The layers were separated. The organic layer was dried over sodium sulfate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by flash-column chromatography (15% ethyl acetate-hexanes initially, grading to 20% ethyl acetate-hexanes) to provide 142 mg of the product, 9-hydroxy-10-methoxy-1-(methoxymethoxy)-3-methyl-8-oxo-5,6,7,8-tetrahydroanthracene-2-carbaldehyde, as an orange foam (74%). 1H NMR (500 MHz, CDCl3): 15.10 (s, 1H), 10.72 (s, 1H), 7.59 (s, 1H), 5.26 (s, 2H), 3.81 (s, 3H), 3.62 (s, 3H), 3.08 (t, 2H, J=6.6 Hz), 2.77 (t, 2H, J=6.6 Hz), 2.73 (s, 3H), 2.12 (m, 2H). 13C NMR (125 MHz, CDCl3): 205.1, 193.2, 163.4, 161.7, 143.1, 141.6, 137.0, 132.4, 126.8, 120.0, 116.4, 111.4, 102.8, 61.1, 58.3, 38.8, 23.7, 22.3, 21.9. FTIR, cm−1: (thin film) 2959 (m), 1674 (m), 1610 (s), 1560 (m), 1375 (s), 1246 (s), 1153 (m), 1038 (s), 1015 (s), 900 (s). HRMS (ESI): Calcd for (C19H20O6+H)+ 345.1333; Found 345.1329. TLC: (20% ethyl acetate-hexanes) Rf=0.22 (CAM).

Workup

  1. temperaturecooled
  2. customthe cooling bath was removed
  3. waitAfter 2.5 h
  4. customthe reaction mixture was partitioned between water (50 mL) and ethyl acetate (100 mL)
  5. customThe layers were separated
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationThe dried solution was filtered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by flash-column chromatography (15% ethyl acetate-hexanes initially

Sources & evidence

ORD record
ord-e65e748b842e4ff5947f7ba040bedd2a
Source dataset
uspto-grants-2015_08
Patent number
US09102697B2

Reaction notes

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