tert-Butyl (3-(3,5-bis(hydroxymethyl)phenoxy)propyl)(isobutyl)carbamate → tert-Butyl (3-(3,5-diformylphenoxy)propyl)(isobutyl)carbamate

HRID 59007Notes

Reaction equation

HRID 59007 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([CH2:25][OH:26])[CH:24]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:25]([C:23]1[CH:22]=[C:5]([CH:4]=[C:3]([CH:2]=[O:1])[CH:24]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:26]

Participants

4

Reactant 2

HCID 131737053tert-Butyl (3-(3,5-bis(hydroxymethyl)phenoxy)propyl)(isobutyl)carbamateHCID 178418287HCID 178418287, compound

Product 1

HCID 131737054tert-Butyl (3-(3,5-diformylphenoxy)propyl)(isobutyl)carbamateYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (3-(3,5-bis(hydroxymethyl)phenoxy)propyl)(isobutyl)carbamate (0.29 g, 0.78 mmol) and CH2Cl2 (20 mL) were added to a round-bottom flask. To the solution was added PCC (0.42 g, 1.94 mmol) and the reaction was stirred for 16 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (90% hexanes/EtOAc) afforded the desired product (0.15 g, 20% 3 steps) as a white semi-solid which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customPurification by column chromatography (90% hexanes/EtOAc)

Sources & evidence

ORD record
ord-a82ad7fc93334dedb520807b71cb2ed6
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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