tert-Butyl acetate → HCID 88583808, compound

HRID 926208Notes

Reaction equation

HRID 926208 reaction equation
[OH:1][C@@H:2]([C:8]1[C:17]([CH3:18])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:27](OC(C)=O)([CH3:30])([CH3:29])[CH3:28]>Cl(O)(=O)(=O)=O>[C:27]([O:1][C@@H:2]([C:8]1[C:17]([CH3:18])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[O:19][S:20]([C:23]([F:26])([F:24])[F:25])(=[O:21])=[O:22])[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 10908tert-Butyl acetateHCID 86691579HCID 86691579, compound

Product 1

HCID 88583808HCID 88583808, compound

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidCatalyst

Procedure

To a stirring solution of (S)-ethyl 2-hydroxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate (560 mg, 1.42 mmol) in t-BuOAc (32.0 mL, 381 mmol) was added 4 drops (catalytic) of 70% HClO4 and the mixture allowed to stir at room temperature for 2 hrs. The mixture was quenched by dumping it into an icy solution of saturated NaHCO3. Extraction with EtOAc (3×20 mL), drying with sodium sulfate and subsequent chromatography on silica gel using EtOAc in Hexanes gave (S)-ethyl 2-tert-butoxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate. 1H-NMR: 400 MHz, (CDCl3): δ 8.06-8.03 (m, 1H); 7.81-7.78 (m, 1H); 7.67 (s, 1H); 7.59-7.53 (m, 2H); 5.73 (s, 1H); 4.25-4.10 (m, 2H); 2.55 (s, 3H); 1.21 (s, 9H), 1.17 (t, 3H).

Workup

  1. customThe mixture was quenched
  2. extractionExtraction with EtOAc (3×20 mL)
  3. dry with materialdrying with sodium sulfate and subsequent chromatography on silica gel

Sources & evidence

ORD record
ord-6ec882d117ce4c31b128eba067d16b0d
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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