Allyl bromide → HCID 124009256, compound

HRID 1471364Notes

Reaction equation

HRID 1471364 reaction equation
[S:1]1[C:5]([CH2:6][C:7]2[C:8]([CH3:25])=[C:9]([CH3:24])[C:10]([OH:23])=[C:11]([CH:13]3[CH:18]([OH:19])[CH:17]([OH:20])[CH2:16][CH:15]([CH2:21][OH:22])[O:14]3)[CH:12]=2)=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:36](Br)[CH:37]=[CH2:38]>CC(C)=O>[CH2:38]([O:23][C:10]1[C:9]([CH3:24])=[C:8]([CH3:25])[C:7]([CH2:6][C:5]2[S:1][C:2]3[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=3[CH:4]=2)=[CH:12][C:11]=1[CH:13]1[CH:18]([OH:19])[CH:17]([OH:20])[CH2:16][CH:15]([CH2:21][OH:22])[O:14]1)[CH:37]=[CH2:36]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 123711362HCID 123711362, compound

Product 1

HCID 124009256HCID 124009256, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 20 ml vial was charged with 22 (33.3 mg, 0.08 mmol) and Cs2CO3 (39.3 mg, 0.12 mmol) and to which was added 1 ml of dry acetone, followed by allyl bromide (19.4 mg, 0.16 mmol). The resulting mixture was stirred at room temperature for 16 h and the solid was filtered of, washed with acetone. The solvent was evaporated and the crude residue was purified by flash column chromatography on silica gel (4 g column, EtOAc/heptane: 0>>>100%) to afford 17.5 mg (43.1%) of 24 as a white solid. 1H NMR (CD3OD) δ 7.71 (d, J=8.08 Hz, 1H), 7.60 (d, J=7.58 Hz, 1H), 7.13-7.28 (m, 3H), 6.87 (s, 1H), 6.14 (m, 1H), 5.47 (dd, J=17.18, 2.02 Hz, 1H), 5.24 (dd, J=10.61, 1.52 Hz, 1H), 4.51 (d, J=9.60 Hz, 1H), 4.47 (dd, J=12.63, 5.05 Hz, 1H), 4.35 (dd, J=12.63, 5.05 Hz, 1H), 4.23 (s, 2H), 3.47-3.73 (5H), 2.23 (s, 3H), 2.20 (s, 3H), 2.01 (m, 1H), 1.48 (q, J=11.12 Hz, 1H). MS (ES) 477.1 (M+Na+).

Workup

  1. filtrationthe solid was filtered of,
  2. washwashed with acetone
  3. customThe solvent was evaporated
  4. customthe crude residue was purified by flash column chromatography on silica gel (4 g column, EtOAc/heptane: 0>>>100%)

Sources & evidence

ORD record
ord-7836919352bc404fbad1f8119dc8664a
Source dataset
uspto-grants-2015_04
Patent number
US09012412B2

Reaction notes

Loading…