Sodium Acetate → HCID 57814789, compound

HRID 1254174Notes

Reaction equation

HRID 1254174 reaction equation
[Cl:1][C@H:2]1[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH3:18])=[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][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH3:18])=[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 57814829HCID 57814829, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57814789HCID 57814789, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 700 mg (1.73 mmol) of alcohol 11 in 4 mL of dichloromethane was added via pipette to a mixture of PCC (700 mg, 3.23 mmol), sodium acetate (350 mg, 4.26 mmol), and Celite (1.3 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 30° C. for 1.5 h. The mixture was worked up by filtration through 20 g of silica gel and washed with 200 mL of 1:4 EA:hexanes. The filtrate was concentrated in vacuo to yield 500 mg) of crude aldehyde 12. Further FCC purification on 10 g of silica gel yielded 380 mg of purified aldehyde 12 (54% yield) as an oil; 1H NMR (CDCl3); 0.93 (t, J=7.2 Hz, 3H), 1.31 (m, 10H), 1.42-1.90 (m, 17H), 1.94-2.44 (m, 4H), 2.28 (t, J=7.5 Hz, 2H), 2.52 (m, 1H), 2.68 (m, 1H), 3.48 (m, 2H), 3.81 (m, 2H), 4.01 (t, J=6.6 Hz, 3H), 4.06 (m, 1H), 4.5-4.64 (m, 2H), 9.75 (m, J=2.1, 9 Hz, 1H).

Workup

  1. washThe pipette was rinsed with an additional 3 mL of DCM
  2. customsealed at 30° C. for 1.5 h
  3. filtrationThe mixture was worked up by filtration through 20 g of silica gel
  4. washwashed with 200 mL of 1:4 EA
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto yield 500 mg) of crude aldehyde 12
  7. customFurther FCC purification on 10 g of silica gel

Sources & evidence

ORD record
ord-c8837e3a9f9a4df586a20f4ab43137b4
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

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