Sodium Acetate → HCID 57845616, compound

HRID 1254169Notes

Reaction equation

HRID 1254169 reaction equation
[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[C@@H:5]([CH2:19][OH:20])[C@H:4]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C([O-])(=O)C.[Na+]>ClCCl>[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[C@@H:5]([CH:19]=[O:20])[C@H:4]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:3]1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 57845584HCID 57845584, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57845616HCID 57845616, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 690 mg (1.72 mmol) of alcohol 4 in 4 mL of dichloromethane was added via pipette to a mixture of PCC (650 mg, 3.0 mmol), sodium acetate (325 mg, 3.96 mmol), and Celite (1.23 g) in 7 mL of DCM. The pipette was rinsed with an additional 3 mL of DCM to complete the transfer. The mixture was stirred sealed at 25° C. for 3 h. The mixture was worked up by filtration through 25 g of silica gel and washed with 200 mL of 1:4 EA:hexanes. The filtrate was concentrated in vacuo to yield 500 mg (72% yield) of crude aldehyde 5 as an oil; 1H NMR (CDCl3): 1.45-1.85 (m, 10H), 2.04-3.00 (m, 10H), 3.51 (m, 1H), 3.81 (m, 1H), 4.07 (m, 1H), 4.59 (m, 4H), 5.26 (m, 1H), 5.45 (m, 1H), 5.92 (m, 1H), 9.75 (dd, J=2.1, 9 Hz, 1H).

Workup

  1. washThe pipette was rinsed with an additional 3 mL of DCM
  2. customsealed at 25° C. for 3 h
  3. filtrationThe mixture was worked up by filtration through 25 g of silica gel
  4. washwashed with 200 mL of 1:4 EA
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0cb6bb1a8fc941a695c7e85ca4502801
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

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