Sodium borohydride → 2-(12,12,12-Trifluorododecyl)benzaldehyde

HRID 1087331Notes

Reaction equation

[F:1][C:2]([F:28])([F:27])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:21]CC(C)(C)N=1.[BH4-].[Na+]>>[F:1][C:2]([F:27])([F:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[O:21]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 198179782-[2-(12,12,12-Trifluorododecyl)phenyl]-4,4-dimethyloxazoline

Product 1

HCID 197651632-(12,12,12-Trifluorododecyl)benzaldehyde

Procedure

Following the procedures of Example 1(a), (b) and (c), 12,12,12-trifluorododecylmagnesium bromide (from 29.19 mmoles of 12,12,12-trifluorododecyl bromide and 25.71 mmoles of magnesium) was reacted with 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (20.17 mmoles) in tetrahydrofuran to give 2-[2-(12,12,12-trifluorododecyl)-phenyl]-4,4-dimethyloxazoline. The oxazoline (14.39 mmoles) was converted to the methiodide salt and then reduced with sodium borohydride (13.43 mmoles) to yield the desired product as an oil.

Sources & evidence

ORD record: ord-c26ae2c294274041af027ee481ab7fb8
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034537

Reaction notes

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