Diisobutylaluminum hydride → HCID 22041389, compound

HRID 1790188Notes

Reaction equation

HRID 1790188 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[CH:12]=2)[CH:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:22][C:20]([F:21])([F:23])[S:17]([O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH2:4][OH:3])[CH:15]=[CH:14]2)(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22002856HCID 22002856, compound

Product 1

HCID 22041389HCID 22041389, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a slurry of 6-trifluoromethanesulfonyloxy-naphthalene-2-carboxylic acid ethyl ester (136.50 g, 0.392 mol) in toluene (1.0 L) at −70° C. was added a solution of DIBAL (1.5 M, 5.75 mL, 0.862 mol) dropwise while maintaining an internal temperature below −55° C. The resulting mixture was allowed to stir for 1 hour and subsequently quenched with acid to pH 5–6 while warming to room temperature. The mixture was extracted with ether (2×). The organics were combined, washed with water (3×), brine and dried (MgSO4). After filtering, the solvents were evaporated and the crude material was purified on silica (eluent: hexane:CH2Cl2, 1:1 to 100% CH2Cl2) to afford 86.0 g (72%) of 6-trifluoromethanesulfonyloxy-naphthalen-2-yl-methanol as an off-white solid. 1H NMR (300 MHz; CDCl3) 2.31 (brs, 1 H), 4.83 (s, 2 H), 7.34 (dd, J1=9.0 Hz, J2=2.0 Hz, 1 H), 7.51 (dd, J1=8.4 Hz, J2=2.0 Hz, 1 H), 7.71 (d, J=2.0 Hz, 1 H), 7.75–7.90 (m, 3 H).

Workup

  1. temperaturewhile maintaining an internal temperature below −55° C
  2. customsubsequently quenched with acid to pH 5–6
  3. extractionThe mixture was extracted with ether (2×)
  4. washwashed with water (3×), brine
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtering
  7. customthe solvents were evaporated
  8. customthe crude material was purified on silica (eluent: hexane:CH2Cl2, 1:1 to 100% CH2Cl2)

Sources & evidence

ORD record
ord-b6cb880dfda64425bb78ed2cb9037e1b
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

Loading…