HCID 722206, compound → HCID 59440796, compound

HRID 1425634Notes

Reaction equation

HRID 1425634 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]([C:18](OC)=[O:19])[CH:11]=[C:12]([CH:17]=2)[C:13](OC)=[O:14])[C:4]([CH3:7])=[CH:5][CH:6]=1.CC(C[Al]CC(C)C)C>C1COCC1>[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:12]([CH2:13][OH:14])[CH:11]=[C:10]([CH2:18][OH:19])[CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 722206HCID 722206, compoundHCID 16682954Dibah

Product 1

HCID 59440796HCID 59440796, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9 (2.87 g, 10 mmol) in THF (60 mL) at −78° C. was added Dibal-H (1 M solution in toluene, 60 mL, 60 mmol) drop wise. The reaction mixture was slowly warmed to room temperature over a period of 6 h, and then quenched by sodium potassium tartrate (1 M, 40 mL). The THF was removed by rotary evaporation, and the resulting aqueous solution was extracted by ether (3×100 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (EtOAc/hexanes, 2:1-4:1) to yield 10 (2.24 g, 97%) as a white solid (Caution: the product is not stable as solution forms, while stable in solid form for weeks at room temperature): 1H NMR (500 MHz, CDCl3) δ 2.01 (s, 6H), 2.45 (s, 2H), 4.69-4.70 (d, J=5.5 Hz, 4H), 5.89 (s, 2H), 7.10 (s, 2H), 7.39 (s, 1H); 13C NMR (125 MHz, CDCl3) δ13.1, 64.5, 105.8, 124.3, 125.6, 128.7, 139.3, 142.4; LC-MS (M+H+) calcd for C14H18NO2 232, found 232.

Workup

  1. customquenched by sodium potassium tartrate (1 M, 40 mL)
  2. customThe THF was removed by rotary evaporation
  3. extractionthe resulting aqueous solution was extracted by ether (3×100 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (EtOAc/hexanes, 2:1-4:1)

Sources & evidence

ORD record
ord-00717ee938d34c49b6e4291105654a03
Source dataset
uspto-grants-2015_01
Patent number
US08932842B2

Reaction notes

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