Trimethylsilyldiazomethane → HCID 23503268, compound

HRID 1835163Notes

Reaction equation

HRID 1835163 reaction equation
[OH:1][CH:2]([C:7]1[O:8][CH:9]=[CH:10][C:11]=1[C:12]([OH:14])=[O:13])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:15][Si:16]([CH:19]=[N+]=[N-])([CH3:18])[CH3:17]>ClCCl>[OH:1][CH:2]([C:7]1[O:8][CH:9]=[CH:10][C:11]=1[C:12]([O:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 23503257HCID 23503257, compound

Product 1

HCID 23503268HCID 23503268, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(1-Hydroxy-3-methylbutyl)furan-3carboxylic acid (800 mg) was dissolved in dichloromethane (30 ml) an d a solution of trimethysilyldiazomethane (2M in hexane, 2.1 ml) was added. The mixture was stirred for 20 h, then diluted with dichloromethane and washed twice with hydrochloric acid. The organic phase was washed with brine, then dried, filtered and evaporated. Chromatography, eluting with diethylether:isohexane (1:1), gave the sub-title compound (435 mg).

Workup

  1. additionwas added
  2. washwashed twice with hydrochloric acid
  3. washThe organic phase was washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. washChromatography, eluting with diethylether:isohexane (1:1)

Sources & evidence

ORD record
ord-aa5eb60f403d4a6ca0f11b109bbbb1d6
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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