Methyl 3-bromopropanoate → 2,2-Dimethyl-4,6-dioxo-5-[3-[(triphenylmethyl)thio]propyl]-1,3-dioxane-5-propanoic acid methylester

HRID 989629Notes

Reaction equation

HRID 989629 reaction equation
[CH3:1][C:2]1([CH3:33])[O:7][C:6](=[O:8])[CH:5]([CH2:9][CH2:10][CH2:11][S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4](=[O:32])[O:3]1.[CH3:34][O:35][C:36](=[O:40])[CH2:37][CH2:38]Br.C[O-].[Na+]>CO.CCCCCC.C(OC(=O)C)C>[CH3:34][O:35][C:36](=[O:40])[CH2:37][CH2:38][C:5]1([CH2:9][CH2:10][CH2:11][S:12][C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:6](=[O:8])[O:7][C:2]([CH3:33])([CH3:1])[O:3][C:4]1=[O:32]

Participants

6

Reactant 3

HCID 76934Methyl 3-bromopropanoateHCID 10942334Sodium MethoxideHCID 111343192,2-Dimethyl-5-(3-((triphenylmethyl)thio]propyl]-1,3-dioxane-4,6-dione

Product 1

HCID 110821512,2-Dimethyl-4,6-dioxo-5-[3-[(triphenylmethyl)thio]propyl]-1,3-dioxane-5-propanoic acid methylesterYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

5 mmol of 2,2-dimethyl-5-[3-[(triphenylmethyl)-thio]-propyl]-1,3-dioxane-5-propanoic-4,6-dione (I) (2.3 g), was dissolved with 20 mmol methyl-3-bromopropionate (3.34g=2.18 ml) and 4.6 ml of 4.37 M methanolic solution of sodium methoxide (20 mmol) in 10 ml of methanol. The reaction mixture was heated to 60° C. overnight after which TLC in hexane/ethylacetate 1:1 detected no starting material. The mixture was then evaporated to dryness and mixed with 40 ml of aqueous 10% KHSO4. The organic material was extracted by 3 portions of EtOAc, the organic layers were combined dried with MgSO4 and evaporated. The residue was crystallized from hexane/ethylacetate to yield 2.1 g (77%) of 2,2-dimethyl-4,6-dioxo-5-[3-[(triphenyl-methyl)thio]propyl]-1,3-dioxane-5-propanoic acid methyl ester (II), 13C-NMR (CDCl3) δ 24.6, 29.4, 29.5, 29.6, 31.4, 32.6, 37.7, 51.9, 52.8, 66.8, 105.7, 126.7, 127.9, 129.5, 144.7, 168.4, 172.0.

Workup

  1. customThe mixture was then evaporated to dryness
  2. additionmixed with 40 ml of aqueous 10% KHSO4
  3. extractionThe organic material was extracted by 3 portions of EtOAc
  4. dry with materialthe organic layers were combined dried with MgSO4
  5. customevaporated
  6. customThe residue was crystallized from hexane/ethylacetate

Sources & evidence

ORD record
ord-1fd2e112be194bf0920477f943aa733f
Source dataset
uspto-grants-2002_10
Patent number
US06458775B1

Reaction notes

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