2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 66915419, compound

HRID 656499Notes

Reaction equation

HRID 656499 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:16].Cl.[C:18]([O-:21])(=[O:20])C.[Na+].[C:23]([Si:27]([CH3:33])([CH3:32])[O:28][CH2:29][CH:30]=O)([CH3:26])([CH3:25])[CH3:24]>C(O)C>[Si:27]([O:28][CH2:29][CH:30]1[C:5]2([C:13]3[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=3)[N:7]([C:18]([O:21][C:5]([CH3:13])([CH3:6])[CH3:4])=[O:20])[C:6]2=[O:16])[CH2:4][CH2:3][CH2:2][NH:1]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 23699784HCID 23699784, compoundHCID 57468508HCID 57468508, compound

Product 1

HCID 66915419HCID 66915419, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1 mol of 3-(3-amino-propyl)-6-methoxy-1,3-dihydro-indol-2-one in 5 ml of ethanol is treated with 5 mmol of sodium acetate hydrochloride and 5 mmol of (tert-butyl-dimethyl-silanyloxy)-acetaldehyde [102191-92-4] and stirred at 60° C. for 3 hours. The reaction mixture is concentrated in vacuo and treated with aqueous saturated potassium carbonate solution and diethyl ether. The phases are separated and the aqueous phase is extracted with diethyl ether (2×). The combined organic phases are washed with water, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additiontreated with aqueous saturated potassium carbonate solution and diethyl ether
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with diethyl ether (2×)
  5. washThe combined organic phases are washed with water
  6. dry with materialdried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-19f03c1c2bf84db39e8cc365266496c7
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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