4-Nitrobenzoyl chloride → [(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]methyl 4-nitrobenzoate

HRID 1643420Notes

Reaction equation

HRID 1643420 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[O:14][C@@H:13]([CH2:15][OH:16])[C:12]([CH3:18])([CH3:17])[CH2:11][O:10]2)=[CH:5][CH:4]=1.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>C(Cl)Cl>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:16][CH2:15][C@H:13]2[C:12]([CH3:18])([CH3:17])[CH2:11][O:10][C@@H:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[O:14]2)=[O:27])=[CH:29][CH:30]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 15858737[(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]methanol

Product 1

HCID 66754235[(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]methyl 4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound obtained in Step B (3.59 g, 14.24 mmol) and TEA (1.98 ml, 14.24 mmol) in DCM (50 ml), 4-Nitrobenzoyl chloride (2.64 g, 14.24 mmol) was added and the reaction was stirred overnight at r.t. The organic phase was washed with a solution of NaH2PO4 5% and brine, dried (MgSO4) and evaporated under reduced pressure. The crude was crystallized from EtOAc at 0° C. adding n-hexane. The product was obtained as a pale yellow solid.

Workup

  1. washThe organic phase was washed with a solution of NaH2PO4 5% and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe crude was crystallized from EtOAc at 0° C.
  5. additionadding n-hexane
  6. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-c600c2484f524205b7b19e09794f0b8d
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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