Chlorotriethylsilane → (S)-ethyl 2-(6-bromo-3-methyl-1-(triethylsilyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

HRID 926188Notes

Reaction equation

HRID 926188 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[C:7]([C@H:13]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]([CH3:24])=[CH:5]2.C(N(C(C)C)CC)(C)C.Cl[Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37])=[C:7]([C@H:13]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]([CH3:24])=[CH:5]2

Participants

5

Reactant 3

HCID 13819ChlorotriethylsilaneHCID 81531DiisopropylethylamineHCID 89681727(S)-ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 89681729(S)-ethyl 2-(6-bromo-3-methyl-1-(triethylsilyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (238 mg, 0.6 mmol) in anhydrous DCM (20 mL) at 0° C. was added diisopropylethylamine (0.21 mL, 1.2 mmol), followed by chlorotriethylsilane (0.12 mL, 0.72 mmol) and the resulting mixture stirred for 1 hour. The reaction was quenched with saturated sodium bicarbonate solution. The mixture was extracted with DCM and organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give the desired compound. 1H NMR (400 MHz, CDCl3): δ 7.82 (m, 2H), 7.42 (m, 1H), 7.08 (s, 1H), 5.98 (s, 1H), 4.19 (m, 2H), 2.43 (s, 3H), 1.21 (s, 9H), 0.98 (t, 9H), 0.83 (m, 6H).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution
  2. extractionThe mixture was extracted with DCM and organic layer
  3. concentrationwas concentrated
  4. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ad394e6d03324e51a2c857732fc4c5c9
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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