HCID 68734484, compound → HCID 131731071, compound

HRID 1910654Notes

Reaction equation

HRID 1910654 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C@@H:20]([OH:32])[C@@H:19]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[O:18][C@H:10]1[O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CS(C)=O.C(OC(=O)C)(=O)C.C(OCC)C>[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:20](=[O:32])[C@@H:19]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[O:18][C@H:10]1[O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:17])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 68734484HCID 68734484, compound

Product 1

HCID 131731071HCID 131731071, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Compound 5.06 (10.5 g, 17.4 mmol) in DMSO (80 mL) and acetic anhydride (60 mL) was heated to 65° C. for 3 h then cooled to room temperature. The reaction mixture was poured into a separatory funnel, diluted with ethyl ether, and washed with H2O. The aqueous layer was back-extracted with additional ethyl ether (5×). The organic layers were combined, dried over Na2SO4, and concentrated in vacuo. The resulting oil was purified by silica gel column chromatography (8% EtOAc/petroleum ether) to afford the title compound (10.4 g, 17.4 mmol, 100%). 1H NMR (500 MHz, CDCl3): δ ppm 7.40-7.34 (m, 6H), 7.32 (d, J=8.3 Hz, 2H), 6.85 (d, J=8.3 Hz, 2H), 4.88 (d, J=7.8 Hz, 1H), 4.86 (d, J=7.8 Hz, 1H), 4.79-4.74 (m, 2H), 4.58 (d, J=11.2 Hz, 1H), 4.15-4.08 (m, 3H), 4.05 (t, J=8.5 Hz, 1H), 3.98 (dd, J=7.1, 3.7 Hz, 1H), 3.85-3.81 (m, 1H), 3.80 (s, 3H), 3.74-3.61 (m, 2H), 1.09-1.02 (m, 2H), 0.93 (s, 9H), 0.11 (s, 6H), 0.06 (s, 9H); 13C NMR (125 MHz, CDCl3): δ ppm 202.00, 159.50, 138.34, 129.89, 129.72, 128.41, 128.12, 127.81, 113.86, 102.52, 83.74, 83.10, 74.75, 73.50, 67.53, 61.74, 55.31, 25.97, 18.46, 18.42, −1.29, −5.17, −5.25; HRMS calcd for C32H54NO7Si2 [M+NH4]+: 620.3439. found 620.3423.

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. washwashed with H2O
  3. extractionThe aqueous layer was back-extracted with additional ethyl ether (5×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified by silica gel column chromatography (8% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-f67b73d2b10a4bf885b228da7e97d3b4
Source dataset
uspto-grants-2013_12
Patent number
US08604004B2

Reaction notes

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