HCID 14913644, compound → HCID 178519098, compound

HRID 1721224Notes

Reaction equation

HRID 1721224 reaction equation
[C:1]([N:20]1[C:24](=[O:25])[CH2:23][O:22][C:21]1=[O:26])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([Li])[CH2:28][CH2:29][CH3:30].Cl[CH2:33][C:34]1[CH:57]=[CH:56][C:37]([O:38][CH2:39][C@H:40]2[CH2:45][CH2:44][C@H:43]([CH2:46][O:47][C:48]3[CH:53]=[CH:52][C:51]([CH2:54]Cl)=[CH:50][CH:49]=3)[CH2:42][CH2:41]2)=[CH:36][CH:35]=1>O1CCCC1.[Cl-].[NH4+]>[C:1]([N:20]1[C:24](=[O:25])[CH:23]([CH2:33][C:34]2[CH:57]=[CH:56][C:37]([O:38][CH2:39][C@H:40]3[CH2:45][CH2:44][C@H:43]([CH2:46][O:47][C:48]4[CH:53]=[CH:52][C:51]([CH2:54][CH:23]5[O:22][C:21](=[O:26])[N:20]([C:30]([C:4]6[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=6)([C:8]6[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=6)[C:29]6[CH:1]=[CH:14][CH:15]=[CH:27][CH:28]=6)[C:24]5=[O:25])=[CH:50][CH:49]=4)[CH2:42][CH2:41]3)=[CH:36][CH:35]=2)[O:22][C:21]1=[O:26])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 14913644HCID 14913644, compoundHCID 178418339ButyllithiumHCID 178478438HCID 178478438, compound

Product 1

HCID 178519098HCID 178519098, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

To 6.8 g of 3-trityl-2,4-oxazolidinedione dissolved in 200 ml of tetrahydrofuran were added 13.6 ml of n-butyllithium and, after 15 minutes of stirring at -78° C., 3.9 g of trans-1,4-bis[(4-chloromethylphenoxy)methyl]cyclohexane which has been dissolved in 20 ml of tetrahydrofuran, followed by additional 2 hours of stirring at -78° C. After completion of the reaction, the reaction mixture was dispersed in saturated ammonium chloride aqueous solution and ice layers and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and then evaporated to dryness, thereby obtaining crude trans-1,4-bis[[4-[(3-trityl-2,4-dioxo-5-oxazolidinyl)methyl]phenoxy]methyl]cyclohexane.

Workup

  1. waitfollowed by additional 2 hours
  2. stirringof stirring at -78° C
  3. customAfter completion of the reaction
  4. extractionice layers and extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c19fb9435780457290ef1423b1a9be70
Source dataset
uspto-grants-1996_04
Patent number
US05508296

Reaction notes

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