Phosphate → HCID 18003073, compound

HRID 567954Notes

Reaction equation

HRID 567954 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2([CH3:18])[CH3:17])(=O)[CH3:2].C(C1C=C2C(CCC2(C)C)=C(C=C)C=1)(C)(C)C.C([N-]C(C)C)(C)C.[Li+].P(Cl)(OCC)(OCC)=O.P([O-])([O-])([O-])=O>>[C:13]([C:11]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:18])[CH3:17])=[C:4]([C:1]#[CH:2])[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 5

HCID 1061PhosphateHCID 13139Diethyl chlorophosphateHCID 61585CelestolideHCID 2724682Lithium diisopropylamide2×HCID 18003086HCID 18003086, compound

Product 1

HCID 18003073HCID 18003073, compound

Procedure

With reference to Table A, 4-acetyl-6-tert-butyl-1,1-dimethylindane (1) is converted into the intermediate 6-tert-butyl-4-ethenyl-1,1-dimethylindane by treatment with lithium diisopropylamide (LDA) and is then treated with an alkyl chlorophosphate, such as diethyl chlorophosphate. The resulting mixed phosphate intermediate is subsequently again treated with LDA and thus results in the 6-tert-butyl-4-ethynyl-1,1-dimethylindane (2).

Sources & evidence

ORD record
ord-16b5ef600cfe44b990cae50b6dd48568
Source dataset
uspto-grants-2001_01
Patent number
US06180674B2

Reaction notes

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