tert-Butanol → HCID 67422763, compound

HRID 1464950Notes

Reaction equation

HRID 1464950 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([C@@H:8]([CH2:42][CH3:43])[C@@H:9]([O:32][C:33](=[O:41])[C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([I:40])[CH:35]=3)[C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2].CC(O)(C)C.[Cl:49]C1C(Cl)=C(I)C=CC=1>C(Cl)Cl>[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([C@@H:8]([CH2:42][CH3:43])[C@@H:9]([O:32][C:33](=[O:41])[C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([I:40])[CH:35]=3)[C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@:14]2([Cl:49])[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 754591,2-Dichloro-3-iodobenzeneHCID 67422286HCID 67422286, compound

Product 1

HCID 67422763HCID 67422763, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4 (3.5 g, 4.95 mmol) in CH2Cl2 (280 ml) containing 0.3 M tBuOH (8.2 ml), dichloroiodobenzene (3.38 g, 12.4 mmol) was added. The mixture was deoxygenated for 3 min by bubbling dry N2. Then the mixture was photolyzed at 0° C. using a tungsten lamps (200 W) for 1 h. The solvent was then evaporated under reduced pressure and the residue was quickly purified by flash chromatography eluting with petroleum ether/EtOAc (8:2, v/v) to yield 3.35 g (4.52 mmol, 92%) of the 17-chloro derivative 5 as white solid.

Workup

  1. additionwas added
  2. customThe mixture was deoxygenated for 3 min
  3. customby bubbling dry N2
  4. customwas photolyzed at 0° C.
  5. customfor 1 h
  6. customThe solvent was then evaporated under reduced pressure
  7. customthe residue was quickly purified by flash chromatography
  8. washeluting with petroleum ether/EtOAc (8:2

Sources & evidence

ORD record
ord-3e8b9dcaf4a74818935d0e63253b0378
Source dataset
uspto-grants-2015_04
Patent number
US08999964B2

Reaction notes

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