Iodoethane → (S)-ethyl 2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)acetate

HRID 514008Notes

Reaction equation

HRID 514008 reaction equation
[CH2:1](I)[CH3:2].[C:4]([O:8][C@@H:9]([C:13]1[C:22]([CH3:23])=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[Cl:24])[C:10]([OH:12])=[O:11])([CH3:7])([CH3:6])[CH3:5].C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[C:4]([O:8][C@@H:9]([C:13]1[C:22]([CH3:23])=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[Cl:24])[C:10]([O:12][CH2:1][CH3:2])=[O:11])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 67126060(S)-2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)acetic acid

Product 1

HCID 68085812(S)-ethyl 2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)acetateYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl iodide (0.35 mL, 1.5 eq.) was added to a mixture of (S)-2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)acetic acid (900 mg, 2.93 mmol, 1 eq.) and Cs2CO3 (1.91 g, 2 eq.) in DMF (920 mL) at room temperature. The reaction mixture was stirred for 1 hour at room temperature. Ethyl acetate was added and organic layer separated and washed with brine (2×). The organic layer was dried (MgSO4) and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give a colorless oil (0.911 g, 93%). 1H-NMR: 300 MHz, (CDCl3) δ: 8.23 (d, 1H), 7.62 (d, 1H), 7.63 (s, 1H), 7.46 (m, 3H), 6.10 (s, 1H), 4.06 (dd, 2H), 2.42 (s, 3H), 1.18 (s, 9H), 1.08 (t, 3H).

Workup

  1. customorganic layer separated
  2. washwashed with brine (2×)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c15f625c0acd47e3963ead972fe1eb57
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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