Bis(4-nitrophenyl) carbonate → HCID 58482076, compound

HRID 1192987Notes

Reaction equation

HRID 1192987 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:11]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)[OH:10])=[CH:5][CH:4]=1)#[CH:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:34](=O)([O:45]C1C=CC([N+]([O-])=O)=CC=1)[O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1>C1COCC1>[C:34](=[O:45])([O:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)[O:10][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:8][CH:7]=1)[CH:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

5

Reactant 3

HCID 78756Bis(4-nitrophenyl) carbonateHCID 2733832Lithium HexamethyldisilazideHCID 58482071HCID 58482071, compound

Product 1

HCID 58482076HCID 58482076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (4-ethynylphenyl)(9H-fluoren-9-yl)methanol (1.0 equivalent) in THF is added to a 1.0 M solution of LiHMDS (1.0 equivalent) in THF at −78° C. After 15 minutes, a solution of bis(4-nitrophenyl) carbonate (1.5 equivalent) is added. The mixture is allowed to warm slowly to ambient temperature, quenched by addition of 1 N HCl, and extracted with ether. The extract is washed sequentially with 1 N HCl, water, and brine, then dried over MgSO4, filtered, and evaporated. The product 4-nitrophenyl carbonate is purified by chromatography on silica gel.

Workup

  1. customquenched by addition of 1 N HCl
  2. extractionextracted with ether
  3. washThe extract is washed sequentially with 1 N HCl, water, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product 4-nitrophenyl carbonate is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-83845398baf348b39f2f30b099da6f8e
Source dataset
uspto-grants-2014_03
Patent number
US08680315B2

Reaction notes

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