Phosphate → HCID 18003073, compound

HRID 478876Notes

Reaction equation

HRID 478876 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-171d423d5ab34d0aaf6e245c52cbf33a
Source dataset
uspto-grants-2003_11
Patent number
US06642273B2

Reaction notes

Loading…