2-Methyl-2-butene → HCID 86698663, compound

HRID 1054659Notes

Reaction equation

HRID 1054659 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][C:27]=2[Cl:28])[NH:24][CH:23]=[C:22]3[CH:29]=[O:30])=[CH:15][CH:14]=1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(=CC)C.Cl([O-])=[O:37].[Na+].O.OP([O-])(O)=O.[Na+].[Cl-].[NH4+]>O1CCCC1.C(O)(C)(C)C.O>[Si:1]([O:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][C:27]=2[Cl:28])[NH:24][CH:23]=[C:22]3[C:29]([OH:37])=[O:30])=[CH:15][CH:14]=1)([CH3:12])[CH3:11])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 105532-Methyl-2-buteneHCID 25517Ammonium ChlorideHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86698664HCID 86698664, compound

Product 1

HCID 86698663HCID 86698663, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-[4-(1-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpropan-2-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde (130 mg, 0.294 mmol) in tetrahydrofuran (2.5 mL) and tert-butanol (2.5 mL) was treated with 2-methyl-2-butene (2.19 mL, 20.6 mmol) followed by a solution of sodium chlorite (496 mg, 5.9 mmol) and sodium phosphate monobasic hydrate (811 mg, 5.9 mmol) in water (2.5 mL) via glass pipet at room temperature. The reaction mixture was stirred vigorously at room temperature for 15 hours, and was poured into saturated aqueous ammonium chloride solution (35 mL). The product was extracted with ethyl acetate (3×25 mL), and the combined organic layers were dried over sodium sulfate, filtered and evaporated to give the title compound as an amber oil. MS (ES−) 456.6 (M−H)−. 1H NMR (400 MHz, CD3OD) δ 8.01 (s, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.57 (s, 1H), 7.43 (d, 2H), 7.37 (d, 2H), 3.63 (s, 2H), 1.36 (s, 6H), 0.86 (s, 9H), −0.05 (s, 6H).

Workup

  1. extractionThe product was extracted with ethyl acetate (3×25 mL)
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-957aad425cc240dbbd7778e194cfefac
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

Loading…