Methanol → HCID 67496553, compound

HRID 1952542Notes

Reaction equation

HRID 1952542 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]#[C:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][OH:17])=[C:11](/[CH:30]=[CH:31]/[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:10]=[C:9]1[C:37]([O:39]CC1C=CC=CC=1)=[O:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOC(C)=O.CO>O.[OH-].[OH-].[Pd+2]>[CH2:1]([N:8]1[C:12]([CH2:13][CH2:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:16][OH:17])=[C:11]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:10]=[C:9]1[C:37]([OH:39])=[O:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 86664859HCID 86664859, compound

Product 1

HCID 67496553HCID 67496553, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

A 25-mL flask was charged with 6 (21 mg, 0.03 mmol), 20% Pd(OH)2 on carbon (nominally 50% in water, 7 mg), and 1 mL each of EtOAc and MeOH. The suspension was stirred under a hydrogen balloon at room temperature for 5-17 hours. The catalyst was filtered off (Celite), the residue concentrated to give 20 mg (quantitative) of a pale yellow foam, which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.30-7.15 (m, 13H), 6.95 (s, 1H), 6.90 (m, 2H), 5.45 (ABq, J=16.4 Hz, 2H), 4.21 (td, J=8.5, 2.1 Hz, 1H), 4.09 (q, J=7.0H, 2H), 3.75 (d, J=8.6 Hz, 1H), 2.72-2.58 (m, 4H), 2.46 (t, J=7.4 Hz, 2H), 1.06-1.51 (m, 2H), 1.48-1.44 (m, 2H), and 1.22 (t, J=7.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 173.45, 165.67, 142.18, 141.36, 139.65, 138.95, 129.11, 128.99, 128.88, 128.72, 128.30, 127.20, 127.15, 126.94, 126.01, 120.86, 120.09, 119.67, 73.09, 60.66, 58.67, 48.23, 35.37, 34.81, 21.23, 20.70, and 14.50; IR (KBr) 3428, 3027, 2933, 1732, 1663, and 1450 cm−1; LRMS-El m/z 481 ([M−CO2+], 64%), 167 ([Ph2CH3+], 75%), and 91 ([PhCH2+], 100%).

Workup

  1. filtrationThe catalyst was filtered off (Celite)
  2. concentrationthe residue concentrated
  3. customto give 20 mg (quantitative) of a pale yellow foam, which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-90a3b9c46cf14342a7fe1eb1c340e612
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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