Ethylparaben → HCID 11175714, compound

HRID 2373466Notes

Reaction equation

HRID 2373466 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([CH2:13][OH:14])=[CH:12][C:5]=2[O:4][CH2:3]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:35]([O:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=1)[CH3:36].CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C(Cl)Cl>[CH2:35]([O:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([O:14][CH2:13][C:11]2[CH:10]=[CH:9][C:6]3[O:7][CH2:8][C:2]([CH3:15])([CH3:1])[CH2:3][O:4][C:5]=3[CH:12]=2)=[CH:41][CH:40]=1)[CH3:36]

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 59852696HCID 59852696, compound

Product 1

HCID 11175714HCID 11175714, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-methanol (31) (100 mg), polymer bound PPh3 (412 mg, ˜3 mmol/g on polystyrene) and ethyl-4-hydroxybenzoate in CH2Cl2 (4 ml) is added di-tert-butylazodicarboxylate (111 mg). The mixture is shaken 1 h, then the polymer is filtered off and the solvent is evaporated. Flash chromatography yields 74 mg of 4-(3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylmethoxy)-benzoic acid ethyl ester as a colourless oil, MS (ESI) 357.2 (M+H)+.

Workup

  1. filtrationthe polymer is filtered off
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-d10b64abbc4047b6a805a8d7c14feb7c
Source dataset
uspto-grants-2008_12
Patent number
US07459480B2

Reaction notes

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