N-Methylmorpholine N-oxide monohydrate → HCID 74027557, compound

HRID 1791055Notes

Reaction equation

HRID 1791055 reaction equation
O.C[N+]1([O-])CCOCC1.[Cl:10][CH:11]=[C:12]1[CH:18]=[CH:17][C:16]2[CH:19]=[C:20]([CH2:23][OH:24])[CH:21]=[CH:22][C:15]=2[O:14][CH2:13]1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:10][CH:11]=[C:12]1[CH:18]=[CH:17][C:16]2[CH:19]=[C:20]([CH:23]=[O:24])[CH:21]=[CH:22][C:15]=2[O:14][CH2:13]1

Participants

5

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 69666864HCID 69666864, compound

Product 1

HCID 74027557HCID 74027557, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

84 mg (0.62 mmol) of 4-methylmorpholine N-oxide monohydrate and 207 mg of 4 Å molecular sieve are added to 92 mg (0.415 mmol) of [3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-yl]methanol, prepared according to example 71, in solution in 1 ml of dichloromethane. 14.6 mg (0.041 mmol) of tetrapropylammonium perruthenate are added to the suspension at 0° C. After stirring at ambient temperature for 1 hour, the reaction medium is purified by chromatography on silica gel (ethyl acetate/heptane 30/70) to give 70 mg (76%) of 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carbaldehyde in the form of a mixture of 2 Z/E isomers in an 85/15 ratio; 1H NMR (300 MHz, CDCl3) Z isomer: 4.90 (s, 2H), 6.41 (m, 3H), 7.14 (d, J=8.3 Hz, 1H), 7.70 (dd, J=8.3 and 2 Hz, 1H), 7.75 (d, J=2.07 Hz, 1H), 9.91 (s, 1H).

Workup

  1. customprepared
  2. customthe reaction medium is purified by chromatography on silica gel (ethyl acetate/heptane 30/70)

Sources & evidence

ORD record
ord-c0b09ff6b9044664bc9097945bc3719f
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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