Sulfuric Acid → HCID 12702707, compound

HRID 1381092Notes

Reaction equation

HRID 1381092 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])/[CH:3]=[CH:4]/[CH:5]([OH:7])[CH3:6].O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O>CCOCC>[CH3:1][Si:2]([CH3:9])([CH3:8])/[CH:3]=[CH:4]/[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516856HCID 516856, compoundHCID 10351819HCID 10351819, compound

Product 1

HCID 12702707HCID 12702707, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Referring to Flowchart II, 3-butyn-2-ol (formula 21) is treated in step H with sodium hydride in ether at -20° C. and then with 2.0 n-butyllithium in hexane, followed by chlorotrimethylsilane, to produce (+)-4-trimethylsilyl-3-butyn-2-ol (formula 22), which is then reacted in step I with lithium aluminum hydride in ether at reflux for several hours, basified and distilled, to produce (±)-trans-4-(trimethylsilyl)-3-buten-2-ol (formula 23). The reaction in step J of (23) in ether with a mixture of sodium dichromate hydrate and sulfuric acid at <5° C. or below produces trans-4-(trimethylsilyl)-3-buten-2-one (formula 24), which upon distillation with selected solvents gives trans-4-(trimethylsilyl)-2-acetoxy-1,3-butadiene (formula 25).

Sources & evidence

ORD record
ord-1f1c0b5e9c3640eeb704d265af60e69e
Source dataset
uspto-grants-1986_04
Patent number
US04585760

Reaction notes

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