Dichloromethane → HCID 67126116, compound

HRID 513997Notes

Reaction equation

HRID 513997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH3:18])[C:9]=2[C@H:19]([OH:22])[CH2:20][OH:21])=[CH:4][CH:3]=1.C(Cl)Cl.[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>N1C=CC=CC=1.C(OCC)(=O)C>[C:26]([O:21][CH2:20][C@H:19]([C:9]1[C:10]([CH3:18])=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[OH:22])(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 62493Pivaloyl chlorideHCID 67126996HCID 67126996, compound

Product 1

HCID 67126116HCID 67126116, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)ethane-1,2-diol (3G) (0.981 g, 3.14 mmol) in pyridine (5.0 mL)/DCM (15.0 mL) was added pivaloyl chloride (0.463 mL, 3.77 mmol). The reaction mixture was stirred for 5 h at room temperature and diluted with ethyl acetate. The organic layer was washed with 1 N HCl, saturated sodium bicarbonate solution, dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexanes) to give 3H as a white solid (1.296 g). 1H-NMR: 300 MHz, (CDCl3): δ: 7.72 (d, J=8.1 Hz, 1H), 7.67 (s, 1H), 7.46-7.37 (m, 3H), 7.26-7.10 (m, 4H), 4.99 (dd, J=8.7, 3.0 Hz, 1H), 4.45 (dd, J=11.7, 9.7 Hz, 1H), 4.13 (dd, J=11.7, 3.3 Hz, 1H), 2.72 (s, 3H), 1.11 (s, 9H).

Workup

  1. washThe organic layer was washed with 1 N HCl, saturated sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexanes)
  6. customto give 3H as a white solid (1.296 g)

Sources & evidence

ORD record
ord-7d763b323dd94cb7815386c730691b1f
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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