Diethyl Ether → HCID 178525620, compound

HRID 879935Notes

Reaction equation

HRID 879935 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[CH2-:5][C:6]([CH3:8])=[O:7].[C:9]([C:12]([C@H:14]([C@@H:16]([C@@H:18]([CH2:20][OH:21])[OH:19])[OH:17])[OH:15])=O)([OH:11])=[O:10].[Si](C=[N+]=[N-])(C)(C)C.C[CH2:30][O:31]CC>CO>[CH2-:1][C:2]([CH3:4])=[O:3].[CH2-:5][C:6]([CH3:8])=[O:7].[C:9]([CH2:12][C:14]([C@H:16]([C@@H:18]([C@@H:20]([CH2:30][OH:31])[OH:21])[OH:19])[OH:17])=[O:15])([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 178526004HCID 178526004, compound

Product 1

HCID 178525620HCID 178525620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The acid (Compound 29) (100 mg, 0.365 mmol) was dissolved in MeOH (3.65 mL, 0.1 M) and cooled to 0° C. After 15 min, 1 M TMSCHN2 in ether (1.82 mL, 5 eq.) was added dropwise via syringe over 15 min. No starting material was detected after 30 min. The reaction was quenched with 5% HOAc/MeOH and the contents evaporated to dryness. Yield: Quant. LRMS (EST+) m/z 289.1 (M+H)+. 1H-NMR (CDCl3) δ: 1.34 (s, 6H), 1.46 (s, 3H), 1.53 (s, 3H), 3.83 (s, 3H), 4.39 (dd, J=2.4 Hz, 5.2 Hz, 1H), 4.59 (dd, J=2.4 Hz, 7.6 Hz, 1H), 4.67 (dd, J=2.4 Hz, 7.6 Hz, 1H), 5.67 (d, J=5.2 Hz).

Workup

  1. waitNo starting material was detected after 30 min
  2. customThe reaction was quenched with 5% HOAc/MeOH
  3. customthe contents evaporated to dryness

Sources & evidence

ORD record
ord-b3e539de45884f2997da8db928a66c40
Source dataset
uspto-grants-2015_03
Patent number
US08993326B2

Reaction notes

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