Selectfluor → HCID 58560636, compound

HRID 571441Notes

Reaction equation

HRID 571441 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:13]=[C:12]2[C:7]=1[C@@H:8]1[CH:26]=[C:25]([CH3:27])[CH2:24][CH2:23][C@H:9]1[C:10]([CH3:22])([CH3:21])[O:11]2)CCC.[B-](F)(F)(F)[F:37].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC(C)=O.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[F:37][C:6]1[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:13]=[C:12]2[C:7]=1[C@@H:8]1[CH:26]=[C:25]([CH3:27])[CH2:24][CH2:23][C@H:9]1[C:10]([CH3:22])([CH3:21])[O:11]2

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 58560640HCID 58560640, compound

Product 1

HCID 58560636HCID 58560636, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 180AcetoneSolvent

Procedure

Tributyl((6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl)stannane (S29) (100 mg, 0.17 mmol, 1 eq.) will be dissolved in acetone (3.5 ml), and AgOTf (87.4 mg, 0.34 mmol, 2 eq.) and Selectfluor (71 mg, 0.20 mmol, 1.2 eq.) will be added at room temperature. The mixture will be stirred for 20 min at room temperature and subsequently concentrated under reduced pressure. The concentrate will be subjected to column chromatography (EtOAc-Hex; 0:100 to 5:95) to give 19.

Workup

  1. concentrationsubsequently concentrated under reduced pressure
  2. concentrationThe concentrate will

Sources & evidence

ORD record
ord-251bf15ff1894ccb8f841d48d6aa31b5
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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