Pivalaldehyde → HCID 69466803, compound

HRID 2298559Notes

Reaction equation

HRID 2298559 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 69466803HCID 69466803, compound

Procedure

Prepared according to the method of paragraph C by reaction of N-propionyl-2-benzoxazolone with trimethylacetaldehyde. Slow addition of the aldehyde to the enolate solution over 1 hour at 0° C. gave a 9:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers. The desired isomer was crystallized from 1:1 ether/hexanes, mp=90-2° C. 1H-NMR (CDCl3, 400 MHz) δ 8.04 (m, 1H), 7.23-7.29 (m, 3H), 4.32 (dq, J=3, 7 Hz, 1H), 3.79 (d, J=10 Hz, 1H), 3.41 (dd, J=3,10 Hz, 1H), 1.51 (d, J=7 Hz, 3H), 0.94 (s, 9H). 13C-NMR (CDCl3, 100 MHz) δ 178.2, 150.8, 142.0, 127.6, 125.7, 125.0, 116.3, 110.0, 84.0, 37.4, 36.2, 26.7, 18.1.

Workup

  1. customPrepared
  2. customgave a 9:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers
  3. customThe desired isomer was crystallized from 1:1 ether/hexanes, mp=90-2° C

Sources & evidence

ORD record
ord-01d87d728cda44e9b307cad7cec8a884
Source dataset
uspto-grants-2002_12
Patent number
US06492562B1

Reaction notes

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