Methanol → HCID 68839974, compound

HRID 1987535Notes

Reaction equation

HRID 1987535 reaction equation
[C:1]1([CH2:7][O:8][C@@H:9]2[C@@H:13]([CH2:14][O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12](OS(C(F)(F)F)(=O)=O)=[CH:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH:34]=[O:35])C.[CH3:36][OH:37].C(N(CC)CC)C>CCCCCC.CCOC(C)=O>[CH3:36][O:37][C:34]([C:12]1[C@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:9]([O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:10][CH:11]=1)=[O:35]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 87593596HCID 87593596, compound

Product 1

HCID 68839974HCID 68839974, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a round bottomed flask equipped with an argon inlet, magnetic stirrer were mixed crude 81 (3.2 g, 5.5 mmol) DMF (25 mL); MeOH (10 mL) and triethylamine (1.54 mL, 11 mmol). Pd(Ph3)4 (635 mg, 0.55 mmol) was added into the solution and the resulting mixture degassed 3 times with CO gas. The reaction was stirred at 1 atmosphere of CO gas at room temperature for 2 h. TLC showed no the absence of starting material. The reaction was worked up with NaOH (0.5 N, 100 mL) at room temperature and extracted with EtOAc (2×50 mL). The combined EtOAc layer was washed with brine (50 mL); dried (Na2SO4) and concentrated in vacuo to afford a light yellow oil. Flash column chromatography (1:2 hexane/EtOAc) gave 7 (1.36 g, 70% over 4 steps).

Workup

  1. customTo a round bottomed flask equipped with an argon inlet, magnetic stirrer
  2. customthe resulting mixture degassed 3 times with CO gas
  3. customwas worked up with NaOH (0.5 N, 100 mL) at room temperature
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe combined EtOAc layer was washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto afford a light yellow oil

Sources & evidence

ORD record
ord-96a20f57fa2c4d0b8cf69c4f97229b88
Source dataset
uspto-grants-2009_06
Patent number
US07550619B2

Reaction notes

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