2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 14623201, compound

HRID 1638434Notes

Reaction equation

HRID 1638434 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.[CH3:11][C:12]1([CH2:33]C(=C2C(=O)OC(C)(C)OC2=O)O)[CH2:17][CH2:16][C:15]2[C:18]([CH3:32])=[C:19]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]([CH3:23])=[C:21]([CH3:22])[C:14]=2[O:13]1>C1(C)C=CC=CC=1>[CH3:10][CH:2]([O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[CH2:33][C:12]1([CH3:11])[CH2:17][CH2:16][C:15]2[C:18]([CH3:32])=[C:19]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]([CH3:23])=[C:21]([CH3:22])[C:14]=2[O:13]1)/[CH:1]=[CH:20]/[CH2:19][C@H:18]([CH3:32])[CH2:15][CH2:16][CH2:17][CH:12]([CH3:33])[CH3:11]

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 70391327HCID 70391327, compound

Product 1

HCID 14623201HCID 14623201, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2.40 % (5.0 mmol) of Meldrum's acid adduct i.e. rac.-5-[2-[3,4-dihydro-2,5,7,8-tetramethyl-6-phenylmethoxy-2H-1-benzopyran-2-yl]-1-hydroxyethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione and 1.19 % (6.0 mmol) of alcohol (2RS,3E,6R) 6,10-dimethyl-3-undecen-2-ol in 4 mL of dry toluene was degassed by 3 cycles of evacuating/purging with argon and then heated under argon to 100° C. CO2 evolution started at ca 90° C. and ceased after ca. 30 minutes. The light yellow solution was stirred for another 2 hours at 100° C. The cooled solution was diluted with hexane, washed with water, sat. NaHCO3 solution and brine, dried over Na2SO4, filtered and evaporated to leave 3.6 g of a brown oil. Chromatography on 250 g of silica gel (hexane/ethyl acetate 5%-6%) afforded 2.33 g (81%) of [2R,S)-3-oxo-4-[3,4-dihydro-2,5,7,8-tetramethylβ-oxo-6-(phenylmethoxy)-2H-1-benzopyran-2-yl-butanoic acid-1,5,9-trimethyl-2-decenyl ester as a colorless very viscous oil.

Workup

  1. customof evacuating/purging with argon
  2. customstarted at ca 90° C.
  3. additionThe cooled solution was diluted with hexane
  4. washwashed with water, sat. NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4882ebabca594f888ea0299509ade3e9
Source dataset
uspto-grants-1989_11
Patent number
US04879395

Reaction notes

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