HCID 11360455, compound → 1,3-Dimethoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-one

HRID 1988219Notes

Reaction equation

HRID 1988219 reaction equation
[CH2:1]([O:7][C:8](=[O:26])[C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:10]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH2:2][CH2:3][CH2:4]C=C>ClCCl>[CH3:16][O:15][C:14]1[C:9]2[C:8](=[O:26])[O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH:25]=[CH:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:10]=2[CH:11]=[C:12]([O:17][CH3:18])[CH:13]=1

Participants

3

Reactant 1

HCID 11360455HCID 11360455, compound

Product 1

HCID 688714241,3-Dimethoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-oneYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of bis(tricyclohexylphosphine)benzylidine ruthenium IV dichloride (39 mg, 0.045 mmol) in dichloromethane (150 ml) at reflux was transferred a solution of 2-hex-5-enyloxy-4,6-dimethoxy-benzoic acid hex-5-enyl ester (430 mg, 1.18 mmol) in dichloromethane (100 ml). After 5 hours at reflux, the solvent was removed and chromatography gave the 1,3-dimethoxy-6,7,8,9,12,13,14,15-octahydro-5,16-dioxa-benzocyclopentadecen-17-one (370 mg).

Workup

  1. temperatureAfter 5 hours at reflux
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-48d89899f37c4abbb355d5d15dff31b4
Source dataset
uspto-grants-2009_06
Patent number
US07553979B2

Reaction notes

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