Trifluoromethanesulfonic acid → HCID 54238537, compound

HRID 1614734Notes

Reaction equation

HRID 1614734 reaction equation
FC(F)(F)S(O)(=O)=[O:4].C[C:10]#[C:11][CH:12]=[CH:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22].[C:23]([O-:26])(O)=O.[Na+]>C(Cl)Cl>[OH:4][C:16]12[C:21](=[O:22])[CH:20]([CH2:19][CH2:18][CH2:17]1)[CH:23]([OH:26])[C:10]#[C:11][CH:12]=[CH:13][C:14]#[C:15]2

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 73824418HCID 73824418, compound

Product 1

HCID 54238537HCID 54238537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethane sulfonic acid (16 ul) was added in one portion to a solution of 65 mg 8-hydroxy-1-TBSoxybicyclo[7.3.1]trideca-4-ene-2,6-diyne-13-one in 20 mL of CH2Cl2 stirring over 1 g of 2A molecular sieves at 25°. The reaction was stirred for 10min and then poured into 10 %aq NaHCO3 and CH2Cl2. The mixture was extracted and the organic extracts were dried over sodium sulfate. Filtration, concentration, and purification by flash chromotography over silica gel using 1:1 diethyl ether/hexane as eluent provided 26mg of the desired 1,8-dihydroxy-bicyclo[7.3.1]trideca-4-ene-2,6-diyne-13-one:

Workup

  1. extractionThe mixture was extracted
  2. dry with materialthe organic extracts were dried over sodium sulfate
  3. filtrationFiltration, concentration, and purification by flash chromotography over silica gel using 1:1 diethyl ether/hexane as eluent

Sources & evidence

ORD record
ord-d0481875d11e4f8b896a673ac18baedd
Source dataset
uspto-grants-1993_03
Patent number
US05198560

Reaction notes

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