Pyridine → 4-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-chloro-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester

HRID 1393697Notes

Reaction equation

HRID 1393697 reaction equation
[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH:17](O)[CH2:16][CH:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]2[CH:27]=[CH:28][CH:29]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:30]([CH3:35])[CH2:31][C:32]#[C:33][CH3:34])[C:8]=1[O:44][CH2:45][O:46][CH3:47].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:75]>CC#N>[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH:17]([Cl:75])[CH2:16][CH:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]2[CH:27]=[CH:28][CH:29]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:30]([CH3:35])[CH2:31][C:32]#[C:33][CH3:34])[C:8]=1[O:44][CH2:45][O:46][CH3:47]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 692154174-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester

Product 1

HCID 692119934-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-chloro-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(3-{3-(tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester of 506 mg (0.72 mmol), triphenyl phosphine (350 mg, 1.34 mmol), CH3CN (6 ml), pyridine (112 mg, 1.42 mmol), and CCl4 (240 mg, 1.55 mmol) was stirred for 12 hours. The reaction solution was concentrated under reduced pressure, and then, subjected to column chromatography on a silica gel to obtain 4-(3-{3-(tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-chloro-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester (426 mg, yield: 82%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9bf2b9dba2a4c4387475ebb21053b60
Source dataset
uspto-grants-2008_03
Patent number
US07345181B2

Reaction notes

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