1-[5-(2-Naphthyl)-1H-imidazol-2-yl]nonane-1,8-dione → 6-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-one

HRID 913058Notes

Reaction equation

HRID 913058 reaction equation
C1C2C(=CC=CC=2)C=CC=1C1NC(C(=O)CCCCCCC(=O)C)=NC=1.[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[C:37]1[N:38]=[CH:39][N:40]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[CH:41]=1.[Li]CCCC.[CH2:55]([C:57]1([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][C:67](N(OC)C)=[O:68])[O:61][CH2:60][CH2:59][O:58]1)[CH3:56]>C1COCC1.CCCCCC.O>[CH2:55]([C:57]1([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][C:67]([C:39]2[N:40]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[CH:41]=[C:37]([C:28]3[CH:29]=[CH:30][C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:27]=3)[N:38]=2)=[O:68])[O:58][CH2:59][CH2:60][O:61]1)[CH3:56]

Participants

8

Reactant 4

HCID 673820661-[5-(2-Naphthyl)-1H-imidazol-2-yl]nonane-1,8-dioneHCID 673822734-(2-Naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazoleHCID 867614186-(2-ethyl-1,3-dioxolan-2-yl)-N-methoxy-N-methylhexanamideHCID 178418339Butyllithium

Product 1

HCID 673819946-(2-ethyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)hexan-1-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of Example 5, E2 (1.0 eq.) in THF (0.1 M solution) at −78° C. was added a solution of n-BuLi (1.3 eq.) in hexane. The solution was stirred for 30 min and then a solution of 6-(2-ethyl-1,3-dioxolan-2-yl)-N-methoxy-N-methylhexanamide (1.5 eq.) in THF was slowly added. The reaction mixture was stirred for 1 hr at −78° C. and then 1 hr at RT. Then water was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was used without purification in the next step. MS (ES) C30H42N2O4Si requires: 523, found: 524 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 1 hr at −78° C.
  2. custom1 hr
  3. customat RT
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was used without purification in the next step

Sources & evidence

ORD record
ord-fdb4b953be124267ae5cbe99ee929abf
Source dataset
uspto-grants-2011_09
Patent number
US08026265B2

Reaction notes

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