Diisopropylethylamine → HCID 71087393, compound

HRID 242374Notes

Reaction equation

HRID 242374 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[CH:8]=[C:7]([CH2:9][OH:10])[N:6]=[CH:5]1.[Si:11](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>ClCCl.CN(C1C=CN=CC=1)C>[Si:11]([O:10][CH2:9][C:7]1[N:6]=[CH:5][N:4]([CH2:3][O:2][CH3:1])[CH:8]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94078tert-Butyldiphenylchlorosilane2×HCID 86674725HCID 86674725, compound

Product 1

HCID 71087393HCID 71087393, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound (8.81 g) obtained in (2) was dissolved in dichloromethane (100 mL), followed by addition of tert-butyldiphenylsilyl chloride (hereinafter, also referred to as TBDPSCl) (24.3 mL), DIEA (21.6 mL) and DMAP (0.760 g) under stirring, and the stirring was continued for 1 day. The reaction solution was concentrated, and the resulting residue was purified by flash chromatography (ethyl acetate/hexane=50%→100%) using silica gel column (product name: Hi-Flash Column 4 L, manufactured by Yamazen Corporation) to afford the title compound (16.9 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe resulting residue was purified by flash chromatography (ethyl acetate/hexane=50%→100%)

Sources & evidence

ORD record
ord-18fc799f84b84a58905d1954346d22fb
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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