Tin tetrachloride → Ethyl 4-[1-(6-methyl-pyrid-3-yl)-3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate

HRID 1862737Notes

Reaction equation

HRID 1862737 reaction equation
[CH3:1][C:2]1S[C:5]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:33])([CH3:32])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1.C[C:35]1C=CC(C2(C=O)C3C(=CC=CC=3)C(C)(C)CC2)=C[N:36]=1.C(OP(C(OC)(OC)CCC1C=CC(C(OCC)=O)=CC=1)(OCC)=O)C.COC(OC)C/C(/C1C=CC(C(OCC)=O)=CC=1)=C\C1C=C2C(C(C)(C)CC=C2C2C=CC(C)=CC=2)=CC=1.Cl[Sn](Cl)(Cl)Cl>ClCCl>[CH3:1][C:2]1[N:36]=[CH:35][C:5]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:33])([CH3:32])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 24287Tin tetrachlorideHCID 18620054Ethyl 4-[1-(5-methyl-thien-2-yl)-3,4-dihydro 4,4-dimethyl-anthracen-8-yl]-benzoate2×HCID 57037360Ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate2×HCID 865886781(2-Methyl-pyrid-5-yl)3,4-dihydro-4,4-dimethyl-naphthaldehyde2×HCID 86588679Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1(tol-4-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethenyl]-benzoate

Product 1

HCID 18620059Ethyl 4-[1-(6-methyl-pyrid-3-yl)-3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is prepared in accordance with the procedure described for the preparation of ethyl 4-[1(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate (Compound 3), from 1(2-methyl-pyrid-5-yl)3,4-dihydro-4,4-dimethyl-naphthaldehyde (Compound K) by reaction with ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D) and proceeding through the intermediate ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethen-1-yl]-benzoate which is cyclized by treatment with SnCl4 in dichloromethane to give the title compoud.

Workup

  1. customThis compound is prepared in accordance with the procedure
  2. customto give the title compoud

Sources & evidence

ORD record
ord-96622237ceba414fbc3cbf7db05cba7d
Source dataset
uspto-grants-2003_03
Patent number
US06538149B1

Reaction notes

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