Sodium Hydroxide → (6-Ethoxy-benzofuran-3-yl)-methanol

HRID 1804790Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:15]=2[O:14][CH:13]=1)=O)C.[OH-].[Na+]>C1COCC1>[CH2:22]([O:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([CH2:10][OH:9])=[CH:13][O:14][C:15]=2[CH:20]=1)[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

1M LiAlH4-solution in THF (47.6 ml, 47.6 mmol) is diluted with 200 ml of THF and cooled to 0° C. 6-Ethoxy-benzofuran-3-carboxylic acid ethyl ester (27a) (5.6 g, 23.8 mmol) is dissolved in 100 ml of THF and added drop wise within 30 min. After completed addition the mixture is allowed to stir at 0° C. for 2 h. Then the reaction mixture is cooled to −15° C. and 10 ml of a 1M NaOH solution is added very slowly. Then the mixture is filtrated over celite, washed with THF and evaporated under reduced pressure.

Workup

additionadded drop wise within 30 min
additionaddition the mixture
temperatureThen the reaction mixture is cooled to −15° C.
filtrationThen the mixture is filtrated over celite
washwashed with THF
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-04a5e50fb54a403ea26e168d592447c7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354431B2

Reaction notes

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