Pivalaldehyde → HCID 69465281, compound

HRID 1794575Notes

Reaction equation

HRID 1794575 reaction equation
[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14])(=[O:4])[CH2:2][CH3:3].[CH3:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18]>>[OH:18][C@@H:17]([C:16]([CH3:20])([CH3:19])[CH3:15])[C@@H:2]([CH3:3])[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14])=[O:4]

Participants

3

Reactant 2

HCID 12417PivalaldehydeHCID 8437913-Propionyl-2-benzoxazolinone

Product 1

HCID 69465281HCID 69465281, compound

Procedure

Prepared according to the method of paragraph C by reaction of N-propionyl-2-benzoxazolone with trimethylacetaldehyde. Rapid addition of the aldehyde to the enolate solution at 0° C. gave a 1:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers. The desired isomer was isolated by silica gel chromatography, then crystallized. 1-NMR (CDCl3, 400 MHz): δ 8.05 (m, 1 H), 7.20–7.27 (m, 4 H), 4.24 (dq, J=7, 4 Hz, 1 H), 3.82 (br t, J=4 Hz, 1 H), 2.33 (br d, J=4 Hz, 1 H), 1.36 (d, J=7 Hz, 3 H), 0.99, (s, 9 H). 13C-NMR (CDCl3, 100 MHz): δ 175.3, 150.8, 142.2, 127.9, 125.4, 124.9, 116.2, 109.9, 77.6, 40.3, 35.8, 29.7, 26.7, 12.7.

Workup

  1. customPrepared
  2. customgave a 1:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers
  3. customThe desired isomer was isolated by silica gel chromatography
  4. customcrystallized

Sources & evidence

ORD record
ord-6381965387ce44fca51cdc772ef01d02
Source dataset
uspto-grants-2006_04
Patent number
US07022825B2

Reaction notes

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