Triethylamine → HCID 59161057, compound

HRID 1873557Notes

Reaction equation

HRID 1873557 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.[C:22]([Si:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)Cl)([CH3:25])([CH3:24])[CH3:23].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[Si:26]([O:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][CH2:6]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 516892Sodium BicarbonateHCID 59161040HCID 59161040, compound

Product 1

HCID 59161057HCID 59161057, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude product from Example 2A is dissolved in 20 ml of dichloromethane, and 0.83 ml (5.93 mmol) of triethylamine and 1.54 ml (5.93 mmol) of tert-butyldiphenylchlorosilane are added. After addition of 24.2 mg (0.20 mmol) of 4-N,N-dimethylaminopyridine the mixture is stirred at RT for 20 h. In each case 10 ml of ethyl acetate and of saturated aqueous sodium bicarbonate solution are then added. The phases are separated, and the combined organic phases are then dried over magnesium sulfate. The solvent is removed on a rotary evaporator and the residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 100:1→20:1).

Workup

  1. customThe phases are separated
  2. dry with materialthe combined organic phases are then dried over magnesium sulfate
  3. customThe solvent is removed on a rotary evaporator
  4. customthe residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 100:1→20:1)

Sources & evidence

ORD record
ord-8d374be8e03f4d31a6b5a2fb71ba5e75
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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