2,2-Dimethoxypropane → 2,2-dimethyl-4-methoxycarbonylmethyl-6-[E-2-(tributylstannyl)ethenyl]-1,3-dioxane

HRID 1587019Notes

Reaction equation

HRID 1587019 reaction equation
[OH:1][CH:2]([CH2:8][CH:9]([OH:25])/[CH:10]=[CH:11]/[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][C:4]([O:6][CH3:7])=[O:5].CO[C:28](OC)([CH3:30])[CH3:29].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[CH3:29][C:28]1([CH3:30])[O:1][CH:2]([CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH2:8][CH:9](/[CH:10]=[CH:11]/[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH2:19][CH3:20])[O:25]1

Participants

6

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86746914E-methyl 3,5-dihydroxy-7-tributylstannyl-6-heptenoate

Product 1

HCID 197598262,2-dimethyl-4-methoxycarbonylmethyl-6-[E-2-(tributylstannyl)ethenyl]-1,3-dioxane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of E-methyl 3,5-dihydroxy-7-tributylstannyl-6-heptenoate (4.18 g), 2,2-dimethoxypropane (18 ml) and pyridinium p-toluene sulfonate (0.227 g) is stirred in anhydrous methylene chloride (4.5 ml) at room temperature for about 20 hours, diluted with ether, washed with saturated sodium bicarbonate solution then saturated sodium chloride solution. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in 10% ether in hexane to give the desired product.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography in 10% ether in hexane

Sources & evidence

ORD record
ord-0322a3d5d9904749807f79acb0eb6e9f
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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