p-Anisoyl chloride → HCID 59736815, compound

HRID 252817Notes

Reaction equation

HRID 252817 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([NH2:21])[CH:20]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>N1C=CC=CC=1>[Si:1]([O:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([NH:21][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[CH:20]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 59736917HCID 59736917, compound

Product 1

HCID 59736815HCID 59736815, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 91 (636 mg, 1.74 mmol) and 4-methoxybenzoyl chloride (446 mg, 2.62 mmol) in pyridine (10 ml) was stirred at room temperature during 16 h. The solvent was evaporated, ethyl acetate was added and washed with a saturated solution of NH4Cl and then with a saturated solution NaCl. The organic layer was dried over MgSO4, filtered and concentrated. After purification by flash chromatography on silica gel (eluent 5-10% EtOAc in Hexanes), 804 mg (93%) of compound 92 was obtained as a yellow oil. 1H NMR: (400 MHz, DMSO) δ (ppm): 10.64 (s, 1H), 8.05 (d, J=8.6 Hz, 1H), 7.95-7.93 (m, 3H), 7.59 (d, J=5.3 Hz, 1H), 7.46 (dd, J=8.6, 2.0 Hz, 1H), 7.28 (d, J=5.3 Hz, 1H), 7.10 (dt, J=9.0, 2.2 Hz, 2H), 4.95 (s, 2H), 3.85 (s, 3H), 0.88 (s, 9H), 0.09 (s, 6H).

Workup

  1. customThe solvent was evaporated
  2. additionethyl acetate was added
  3. washwashed with a saturated solution of NH4Cl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter purification by flash chromatography on silica gel (eluent 5-10% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-79aca3fe6c784c429e85f6cc6f3874ce
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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