Acetic Anhydride → HCID 22165551, compound

HRID 1032280Notes

Reaction equation

[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:7][CH:6]=[C:5]([CH:8]=[O:9])[CH:4]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:20][C:21](=[O:34])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:35](OC(=O)C)(=[O:37])[CH3:36]>>[C:35]([O:9][CH:8]([C:5]1[CH:4]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:7][CH:6]=1)[CH2:20][C:21](=[O:34])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:37])[CH3:36]

Participants

Reactant 4

HCID 7918Acetic Anhydride

HCID 75364Tetradecan-2-one

HCID 2724682Lithium diisopropylamide

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 22165551HCID 22165551, compound

Procedure

5-Trimethylsilyl-3-furaldehyde is treated with lithium diisopropylamide and 2-tetradecanone, followed by acetic anhydride to give 3-(1-acetoxy-3-ketopentadecanyl)-5-trimethylsilylfuran. Oxidation by the method described in Example 1 gives 4-(1-acetoxy-3-ketopentadecanyl)-5-hydroxy-2(5H)-furanone.

Sources & evidence

ORD record: ord-45ebd511a339402bbc75a66efc380832
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04957917

Reaction notes

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