Acetic Anhydride → 6-(t-Butyldimethylsilyloxy)-1-hexyne

HRID 333501Notes

Reaction equation

HRID 333501 reaction equation
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12]CO)([CH3:4])([CH3:3])[CH3:2].C([Si](C)(C)OCCCCC#CCOC(=O)C)(C)(C)C.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:1]([Si:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12])([CH3:15])[CH3:16])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 111725557-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol2×HCID 86593935Acetic acid 7-(tert-butyl-dimethyl-silanyloxy)-hept-2-ynyl ester

Product 1

HCID 110094486-(t-Butyldimethylsilyloxy)-1-hexyne

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol (27); and Acetic acid 7-(tert-butyl-dimethyl-silanyloxy)-hept-2-ynyl ester (28, FIG. 4). A solution of 7-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol (27) (4.507 g, 21 mmol) in pyridine (20 mL) was treated with acetic anhydride (3.0 mL, 31.8 mmol). After 18 hours, the solvent was evaporated and the residue co-evaporated with toluene. The residue was used directly in the next step.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-aed88edf72c04aadae96bb7fbb2ba296
Source dataset
uspto-grants-2014_11
Patent number
US08883139B2

Reaction notes

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