1-(tert-Butyldiphenylsilyl)oxy-dodecan-12-ol → 1-(tert-Butyldiphenylsilyl)oxy-10,12-Docosadiyne-22-ol

HRID 333507

Reaction equation

HRID 333507 reaction equation
[Si:1]([O:18][CH2:19][CH2:20]CCCCCCCCCCO)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]#[C:42][C:43]#[C:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][OH:54]>>[Si:1]([O:18][CH2:19][CH2:20][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]#[C:42][C:43]#[C:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][OH:54])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 110156841-(tert-Butyldiphenylsilyl)oxy-dodecan-12-olHCID 1459565710,12-Docosadiyne-1,22-diol

Product 1

HCID 866536121-(tert-Butyldiphenylsilyl)oxy-10,12-Docosadiyne-22-olYield 26%

Procedure

This substance was synthesized following the same procedure as for (1) and obtained in comparable yields using 9.40 g of (3) (28.1 mmol) as diol component. 4.25 g of 1-(tert-Butyldiphenylsilyl)oxy-10,12-Docosadiyne-22-ol (7.24 mmol) was obtained in a yield of 26%. 1H NMR (250.13 MHz): δ (ppm)=1.05 (s, 9H, tert-butyl), 1.26 (br, 20H, —CH2—CH2—CH2—CH2—CH2—), 1.53 (m, 8H, —O—CH2—CH2— and —C≡C—CH2—CH2—), 2.24 (t, 4H, 3J=6.8 Hz, —C≡C—CH2—), 3.64 (t, 2H, 3J=6.5 Hz, —Si—O—CH2), 3.65 (t, 2H, 3J=6.5 Hz, HO—CH2—), 7.40 (m, 6H, phenyl), 7.69 (m, 4H, phenyl). 13C NMR (75.48 MHz): δ (ppm)=25.69, 25.72, 26.9, 28.30, 28.34, 28.8, 29.00, 29.04, 29.30, 29.34, 29.4, 32.5, 32.8, 63.1, 64.0, 127.5, 129.5, 134.1, 135.6.

Workup

  1. customThis substance was synthesized
  2. customobtained
  3. customin comparable yields

Sources & evidence

ORD record
ord-81f4580e02624c5993a3abc5062b6306
Source dataset
uspto-grants-2014_11
Patent number
US08883211B2

Linked notes

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