Acetyl chloride → 1-[5-Chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1095142Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)=[C:6]([CH:9]=1)[CH:7]=O.C(OC([N:28]1CCC(COC2C=CC(I)=CC=2C=O)[CH2:30][CH2:29]1)=O)(C)(C)C.[CH3:45][Si:46](N[Si](C)(C)C)([CH3:48])[CH3:47].C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=[O:73])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)=[C:6]([CH:7]=[N:28][C:29]([O:73][Si:46]([CH3:48])([CH3:47])[CH3:45])=[CH2:30])[CH:9]=1

Participants

Reactant 7

HCID 6367Acetyl chloride

HCID 6397Chlorotrimethylsilane

HCID 8471Triethylamine

HCID 13838Hexamethyldisilazane

HCID 577431634-(2-Formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester

HCID 577432965-Chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-benzaldehyde

HCID 178418339Butyllithium

Product 1

HCID 666415361-[5-Chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Procedure

In a manner similar to the method described in example 1d, 5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-benzaldehyde (1.5 g, 5 mmol) was used as the starting material in place of 4-(2-formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester to react with 1,1,3,3,3-hexamethyldisilazane (0.8 g, 5 mmol), n-butyllithium (2.5 M, 2 mL, 5 mmol), trimethylsilyl chloride (0.55 g, 5 mmol), triethylamine (0.7 g, 6.8 mmol) and acetyl chloride (0.5 g, 6.8 mmol) to give crude 1-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Sources & evidence

ORD record: ord-6d3b335b08c14016b052ccabd28f1b99
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08134001B2

Reaction notes

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