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Methyl Salicylate → 2-(methoxycarbonyl)phenyl 2,3-dihydro-5,8-dimethylspiro[4H-1-benzothiopyran-4,2'-[1,3]dioxolane]-6-carboxylate 1,1-dioxide

HRID 393909
Notes
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Reaction equation

HRID 393909 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:19])[C:5]2[S:16](=[O:18])(=[O:17])[CH2:15][CH2:14][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[C:6]=2[C:7]=1C.C(N([CH2:25][CH3:26])CC)C.[C:27]([O:36][CH3:37])(=[O:35])[C:28]1[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[OH:30].[C]=[O:39]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:2][C:7]1[C:6]2[C:9]3([CH2:14][CH2:15][S:16](=[O:18])(=[O:17])[C:5]=2[C:4]([CH3:19])=[CH:3][C:26]=1[C:25]([O:30][C:29]1[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=1[C:27]([O:36][CH3:37])=[O:35])=[O:39])[O:13][CH2:12][CH2:11][O:10]3
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4133Methyl SalicylateHCID 8471TriethylamineHCID 22648325HCID 22648325, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 226483282-(methoxycarbonyl)phenyl 2,3-dihydro-5,8-dimethylspiro[4H-1-benzothiopyran-4,2'-[1,3]dioxolane]-6-carboxylate 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A Fisher-Porter tube (defined in Example 3A) was charged with 3.94 g (10 mmol) of 2,3-dihydro-6-iodo-5,8-dimethylspiro[4H-1-benzothiopyran-4,2′-[1,3]dioxolane] 1,1-dioxide, 1.53 g (15 mmol) of triethylamine, 23 mg (0.1 mmol) of palladium acetate, 1.67 g (11 mmol) of methyl salicylate, and 20 mL of DMF. The mixture was heated for 3 hr at 80° C. followed by 17 hr at 50° C. in a carbon monoxide atmosphere at 70 psi (4.8×105 Pa). The mixture was poured into 150 mL of ice water and filtered. The solid was washed with 10 mL of water, 10 mL of acetonitrile, and 10 mL of diethyl ether to give the title product as 3.50 g of pink solid, m.p. 179-181° C. 1H NMR (CDCl3): δ 2.58 (s, 3), 2.60 (m, 2), 2.84 (s, 3), 3.52 (m, 2), 3.84 (s, 3), 4.19 (m, 2), 4.34 (m, 2), 7.20 (d, 1), 7.36 (t, 1), 7.61 (t, 1), 8.02 (s, 1), 8.08 (d, 1).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with 10 mL of water, 10 mL of acetonitrile, and 10 mL of diethyl ether

Sources & evidence

ORD record
ord-442471aec4014ab985317d76aa5b6fbe
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06809206B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes