HCID 13240723, compound → HCID 13240749, compound

HRID 1776964Notes

Reaction equation

HRID 1776964 reaction equation
[CH:1]1([CH2:16][OH:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[CH:1]1([CH:16]=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 13240723HCID 13240723, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13240749HCID 13240749, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol 52 (300 mg, 1.25 mmol) in CH2Cl2 (20 mL) was added PCC (404 mg, 1.87 mmol) at room temperature. The reaction was monitored by TLC (50% hexanes/50% CH2Cl2) until complete (60 min) Upon reaching completion, the mixture was then diluted with Et2O, filtered through Celite and concentrated in vacuo to give aldehyde 53 as a yellow oil that was used without further purification (250 mg crude). 1H NMR (CDCl3) δ 9.61 (s, 1H), 2.43 (m, 2H), 2.29 (m, 1H), 1.62 (m, 4H), 1.49 (m, 4H), 1.44-1.31 (m, 20H). This aldehyde was found to be unstable and was best used immediately in subsequent steps.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c390dda381e14b079e535d12bbf166ad
Source dataset
uspto-grants-2016_02
Patent number
US09266815B2

Reaction notes

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