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

HRID 338316Notes

Reaction equation

HRID 338316 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.

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-b414a741e61f4ef5a38066bc8e6a2da1
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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