HCID 22041389, compound → HCID 22041384, compound

HRID 1790189Notes

Reaction equation

HRID 1790189 reaction equation
[F:1][C:2]([F:20])([F:19])[S:3]([O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][OH:18])[CH:11]=[CH:10]2)(=[O:5])=[O:4].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[F:19][C:2]([F:1])([F:20])[S:3]([O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]=[O:18])[CH:11]=[CH:10]2)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 22041389HCID 22041389, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22041384HCID 22041384, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mechanical stirred solution of 6-trifluoromethanesulfonyloxy-naphthalen-2-yl-methanol (70.0 g, 0.228 mol) in CH2Cl2 (600 mL) under an atmosphere of argon was added PCC (54.20 g, 0.25 mol, crushed prior to addition) over a few minutes. After 2 hours the resulting black suspension was poured onto a silica gel column and purified using CH2Cl2 to give a yellow oil that slowly crystallized upon standing to afford 65.1 g (94%) of 6-trifluoromethanesulfonyloxy-naphthalene-2-carboxaldehyde. 1H NMR (300 MHz; CDCl3) 7.50 (dd, J1=9.0 Hz, J2=2.0 Hz, 1 H), 7.83 (d, J=2.0 Hz, 1 H), 7.99 (d, J=8.4 Hz, 1 H), 7.07 (dd, J1=9.0 Hz, J2=2.0 Hz, 1 H), 8.12 (d, J=9.0 Hz, 1 H), 8.40 (brs, 1 H), 10.19 (s, 1 H), 13C NMR (75 MHz, CDCl3) 118.7 (q, J=318 Hz), 119.5, 120.9, 124.5, 129.1, 131.6, 132.2, 133.6, 134.9, 136.4, 148.9, 191.4.

Workup

  1. customcrushed
  2. additionto addition) over a few minutes
  3. additionAfter 2 hours the resulting black suspension was poured onto a silica gel column
  4. custompurified
  5. customto give a yellow oil that
  6. customslowly crystallized

Sources & evidence

ORD record
ord-69ef83815cd34e009ed65d285bc956f6
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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