Tin tetrachloride → (2-Naphthalen-2-ylmethyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-methoxy-phenyl)-methanone

HRID 1871302Notes

Reaction equation

HRID 1871302 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]=1[O:13][CH3:14])[C:7]([OH:9])=O)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[CH2:39][C:40]1[O:41][C:42]([CH3:46])=[C:43]([CH3:45])[CH:44]=1>CN(C)C=O.C(Cl)Cl>[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[CH2:39][C:40]1[O:41][C:42]([CH3:46])=[C:43]([CH3:45])[C:44]=1[C:7]([C:6]1[CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]([O:13][CH3:14])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)=[O:9]

Participants

7

Reactant 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 15895030HCID 15895030, compoundHCID 234456112-Naphthalen-2-ylmethyl-4,5-dimethylfuran

Product 1

HCID 23445617(2-Naphthalen-2-ylmethyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-methoxy-phenyl)-methanoneYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 2 using 3,5-diisopropyl-p-anisic acid (0.93 g, 3.95 mmol, RN-117439-59-5), oxalyl chloride (0.377 mL, 4.33 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (0.507 mL, 4.33 mmol) and 2-naphthalen-2-ylmethyl-4,5-dimethylfuran (0.93 g, 3.94 inmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with a 2 & 4% EtOAc/pet. ether step gradient gave 0.357 g (20%) of the title compound. 1H NMR (DMSO-d6) δ 1.14 (d, 12 H), 1.82 (s, 3 H), 2.20 (s, 3 H), 3.27 (septet, 2 H), 3.74 (s, 3 H), 4.02 (s, 2 H), 7.19 (dd, 1 H), 7.45-7.52 (m, 5 H), 7.76-7.79 (m, 3 H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with a 2 & 4% EtOAc/pet. ether step gradient

Sources & evidence

ORD record
ord-709020a9c2994e3bbd924fbf42cc84d4
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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