Sodium Hydroxide → (S)-2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)ethanol

HRID 514007Notes

Reaction equation

HRID 514007 reaction equation
C([O:7][CH2:8][C@@H:9]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[Cl:21])(=O)C(C)(C)C.[OH-].[Na+]>CO.C1COCC1.C(OCC)(=O)C>[C:23]([O:22][C@@H:9]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[Cl:21])[CH2:8][OH:7])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67126074(S)-2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)ethyl pivalate

Product 1

HCID 67126182(S)-2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)ethanolYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-tert-Butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)ethyl pivalate (4G, 1.72 g, 4.56 mmol) was dissolved in MeOH (10 mL) and THF (10 mL). Sodium hydroxide (2 M, 9.13 mL) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The aqueous layer was back-extracted with ethyl acetate and the combined organics were dried (MgSO4), concentrated in vacuo and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give a colorless liquid (1.12 g, 84%). 1H-NMR: 300 MHz, (CD3OD) δ: 8.23 (d, 1H), 7.78 (d, 1H), 7.60 (s, 1H), 7.52 (dd, 2H), 5.69 (m, 1H), 3.83 (dd, 1H), 3.61 (m, 1H), 2.71 (s, 3H), 1.18 (s, 9H).

Workup

  1. washwashed with brine
  2. extractionThe aqueous layer was back-extracted with ethyl acetate
  3. dry with materialthe combined organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-deed2030fa0f4a00ab83a744d1eb60ed
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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