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

HRID 842598Notes

Reaction equation

HRID 842598 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 (3.34 g=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-[(triphenylmethyl)thio]propyl]-1,3-dioxane-5-propanoic acid methyl ester (II), 13C-NMR (CDCl3) δ24.6, 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-6c19afc04ca34b6a9340a47b53d03333
Source dataset
uspto-grants-2002_04
Patent number
US06376478B1

Reaction notes

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